Method for producing phosphorus compound

Abstract

To provide a novel production method by which a wide range of phosphorus compounds can be efficiently produced through a simple process.SOLUTION: There is provided a method for producing a phosphorus compound represented by the following chemical formula (C), comprising a step (I) of reacting a silyl phosphate ester represented by the following chemical formula (A) with a compound represented by the following chemical formula (B).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a method for producing a phosphorus compound. [Background technology]

[0002] Fluorine-containing phosphate esters are used in a wide range of applications, including water- and oil-repellent agents for fibers, paper, etc., surfactants, release agents, metal surface treatment agents, resin curing agents, lubricating oil additives, antistatic agents, flame retardant agents, rust inhibitors for grease, cosmetics, oral preparations, and additives for non-aqueous electrolytes for secondary batteries, and a variety of methods for producing fluorine-containing phosphate esters have been developed to suit each application (Patent Documents 1 to 6).

[0003] For example, Patent Document 5 discloses a production example of a method for producing a monofluorophosphate ester salt as a fluorine-containing phosphate ester. According to this production method, a metal salt such as lithium chloride or calcium carbonate is mixed with phosphoryl chloride in a solvent, and this mixture is reacted in turn with water, absolute alcohol, and an organic solvent solution of hydrogen fluoride to produce a monofluorophosphate ester salt. However, with this production method, it is difficult to selectively obtain only the monofluorophosphate ester salt, and by-products other than the monofluorophosphate ester salt are produced, which is thought to require a complicated purification step.

[0004] Patent Document 6 discloses a method for producing a monofluorophosphate salt as a fluorine-containing phosphate ester. According to this production method, a monohalophosphate diester is fluorinated to produce a monofluorophosphate diester, and then the monofluorophosphate diester is reacted with a halide such as lithium chloride or sodium iodide to produce a monofluorophosphate salt. However, this production method requires the acquisition of a monohalophosphate diester as a raw material, and it is very difficult to obtain a monohalophosphate diester having a long-chain hydrocarbon group or a complex hydrocarbon group. In addition, the step of reacting a monofluorophosphate diester with a halide is carried out by S NIt is considered that this reaction is a two-step reaction, and it is presumed that it is difficult to apply this reaction to diphenyl fluorophosphate, etc., which has an aromatic hydrocarbon group. Therefore, the type of monofluorophosphate ester salt that can be produced by the method for producing a monofluorophosphate ester salt described in Patent Document 6 is limited. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Japanese Patent Application Publication No. 5-222070 [Patent Document 2] Japanese Patent Application Publication No. 5-194560 [Patent Document 3] Japanese Patent Application Publication No. 1-268696 [Patent Document 4] Japanese Patent Application Publication No. 4-235908 [Patent Document 5] Patent No. 6600631 [Patent Document 6] Patent No. 6925604 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention has been made in consideration of the above-mentioned problems, and an object of the present invention is to provide a novel production method that enables a wide variety of phosphorus compounds to be produced efficiently by a simple method. [Means for solving the problem]

[0007] The present invention relates to the following [1] to [3]. [1] A method for producing a phosphorus compound represented by the following chemical formula (C), comprising step (I) of reacting a phosphate silyl ester represented by the following chemical formula (A) with a compound represented by the following chemical formula (B): [ka] [Wherein, R 1 ~R3 are each independently a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond, or an alkoxy group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond. 1 R 4 group or -Y 2 -ZY 3 represents a H group. 1 ~Y 3 are each independently an oxygen atom, a sulfur atom, or an imino group (NR 5 ) and the R 4 , and R 5 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond, and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond. [ka] [Wherein, R 6 represents a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond; 4 is an oxygen atom, a sulfur atom, or an imino group (NR 7 ) and the R 7 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a heteroatom, or an unsaturated bond, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium. n represents the valence of the cation. [ka] [Wherein, M and Y 4 , R 6 , X, and n are the same as those in the chemical formulas (A) and (B). [2] A method for producing a phosphoric acid compound represented by the following chemical formula (D), comprising a step (I') of intramolecularly reacting a phosphoric acid silyl ester represented by the following chemical formula (A'): [ka] [Wherein, R 1 ~R 3 are each independently a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond, or an alkoxy group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond. 2 and Y 3 are each independently an oxygen atom, a sulfur atom, or an imino group (NR 5 ), wherein Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond. [ka] [Wherein, the Y 2 , Y 3 , Z are the same as those in the chemical formula (A'). [3] A method for producing a phosphorus compound represented by the following chemical formula (F) or (G), comprising step (II) of reacting a phosphorus compound represented by the following chemical formula (C') or a phosphorus compound represented by the following chemical formula (D) with a salt consisting of a cation and an anion represented by the following chemical formula (E). [ka] [Wherein, R 6represents a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond; 4 is an oxygen atom, a sulfur atom, or an imino group (NR 7 ) and the R 7 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond. 1 R 4 group or -Y 2 -ZY 3 represents a H group. 1 ~Y 3 are each independently an oxygen atom, a sulfur atom, or an imino group (NR 5 ) and the R 4 , and R 5 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond, and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond. [ka] [Wherein, the Y 2 and Y 3 are each independently an oxygen atom, a sulfur atom, or an imino group (NR 5 ) and the R 5 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond, and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond. [ka] [In the formula, M' represents an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium. Q represents a hydroxide, a carbonate, a hydrogen carbonate, an oxide, or a halogen atom. n represents the valence of a cation, and m represents the valence of an anion.] [ka] [Wherein, M' and Y 4 , R 6 , X, and n are the same as those in the chemical formulas (C') and (E). [ka] [Wherein, M' and Y 2 , Y 3 , Z, and n are the same as those in the chemical formulas (D) and (E). [Effects of the Invention]

[0008] According to the present invention, a novel production method can be provided that enables a wide variety of phosphorus compounds to be produced simply and efficiently. DETAILED DESCRIPTION OF THE INVENTION

[0009] (Method for producing phosphorus compound in step (I)) The method for producing a phosphorus compound according to this embodiment will be described below. The method for producing a phosphorus compound of this embodiment includes a step (I) of reacting a silyl phosphate ester represented by chemical formula (A) with a compound represented by chemical formula (B), as shown in the chemical reaction formula below, and can produce a phosphorus compound represented by chemical formula (C).

[0010] [ka]

[0011] The basic reaction mechanism of step (I) is assumed to be as follows:4 The following will be described by taking as an example an embodiment in which is an oxygen atom, the M is a hydrogen atom, and n is 1. First, the lone electron pair of O in the chemical formula (B) nucleophilically attacks P in the chemical formula (A), and then F, which is easily bonded to P, is eliminated, resulting in -OR 6 The group is replaced by F. Then, the free F - attacks Si in the chemical formula (A), which is likely to form a bond with F, and R 1 R 2 R 3 It is believed that the phosphorus compound represented by the above chemical formula (C) is produced by elimination as Si—F.

[0012] [ka]

[0013] As for the advantages obtained by silylation of a fluorine-containing phosphorus compound, such as the phosphate silyl ester represented by the chemical formula (A), in addition to the fact that the reaction mechanism can be utilized, several advantages are assumed. For ease of understanding, for example, a difluorophosphate silyl ester in which X in the chemical formula (A) is represented by a fluorine atom and -SiR in the difluorophosphate silyl ester are shown below. 1 R 2 R 3 The first is the improved reactivity with the compound represented by the chemical formula (B). Specifically, when comparing the difference in the susceptibility to nucleophilic attack at P in the two compounds from the perspective of the difference in LUMO energy at P, the former is a compound with a PO-Si covalent bond, while the latter is a compound with a PO - …H +The latter, which can be stabilized as an anion, has a higher LUMO energy at P, while the former has a lower LUMO energy at P. In other words, silylation of difluorophosphoric acid lowers the LUMO energy at P, making it more susceptible to nucleophilic attack and facilitating the reaction, which is thought to lead to improved reactivity. The second advantage is that purification by distillation or other methods is relatively easy. Specifically, difluorophosphoric acid contains an -OH group, which forms strong hydrogen bonds between molecules, resulting in low volatility and a high boiling point, making purification by distillation or other methods difficult. On the other hand, difluorophosphate silyl ester loses its -OH group upon silylation, preventing the formation of strong hydrogen bonds between molecules. This increases volatility and lowers the boiling point compared to difluorophosphoric acid, which is thought to make purification by distillation or other methods relatively easy.

[0014] Furthermore, for example, when X in the chemical formula (A) is a difluorophosphate silyl ester represented by a fluorine atom, Y in the chemical formula (B) 4 is an oxygen atom, M is a hydrogen atom, and n is 1, to form a compound in which X in the chemical formula (C) is a fluorine atom and Y 4 The monofluorophosphate ester represented by R is produced with good selectivity. In other words, this means that the phosphate diester produced when the produced monofluorophosphate ester further reacts with the compound represented by the chemical formula (B) is unlikely to be produced. Basically, as shown in the reaction mechanism above, 1 R 2 R 3 This is thought to be because the Si-F elimination acts as a driving force, causing the reaction to proceed rapidly, but other factors are also suspected. For example, based on the same reasoning as above, the difference in the susceptibility of the starting material, difluorophosphate silyl ester, and the resulting monofluorophosphate ester to nucleophilic attack at P can be explained by the difference in LUMO energy at P. The former is a compound with a PO-Si covalent bond, while the latter is a compound with a PO- …H + The latter, which can be stabilized as an anion, has a higher LUMO energy, while the LUMO energy at P of the former is lower than that of the latter. In other words, it is thought that the former is susceptible to nucleophilic attack by P, while the latter is less susceptible to nucleophilic attack by P. Therefore, in the nucleophilic attack from the compound represented by chemical formula (B), the reaction proceeds quickly from the former difluorophosphate silyl ester, which is susceptible to nucleophilic attack, to produce the latter monofluorophosphate ester, but the reaction does not proceed smoothly to produce the phosphate diester, which is produced when the reaction proceeds further from the latter monofluorophosphate ester compound, which is less susceptible to nucleophilic attack, and it is thought that this is why the monofluorophosphate ester is produced with good selectivity.

[0015] As mentioned above, it is presumed that the reaction between a monofluorophosphate ester and a compound represented by the chemical formula (B) does not proceed easily. However, based on the advantages obtained by silylation of a fluorine-containing phosphorus compound as described above, by silylation of the monofluorophosphate ester, it is possible to further react it with a compound represented by the chemical formula (B), thereby producing a symmetric or asymmetric phosphate diester. Specifically, for example, when X in the chemical formula (A) is -Y 1 R 4 group, and said Y 1 is represented by an oxygen atom, the Y in the chemical formula (B) 4 When a compound represented by the formula (C) is reacted with a compound represented by the formula (C) in which X is -OR, 4 group, the Y 4 is an oxygen atom and the M is a hydrogen atom, the phosphoric acid diester is produced with good reactivity, and R of the phosphoric acid diester 4 and R 6 If they are the same, a symmetrical phosphate diester can be produced; if they are different, an asymmetrical phosphate diester can be produced.

[0016] <Phosphate silyl ester> The silyl phosphate ester is represented by the following chemical formula (A):

[0017] [ka]

[0018] In the chemical formula (A), the R 1 ~R 3 each independently represent a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond (hereinafter sometimes referred to as a "hydrocarbon group having a halogen atom, etc."), or an alkoxy group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond (hereinafter sometimes referred to as an "alkoxy group having a halogen atom, etc.").

[0019] In this specification, halogen atoms refer to fluorine, chlorine, bromine and iodine atoms, and heteroatoms refer to oxygen, nitrogen, sulfur, phosphorus and other atoms.

[0020] In this specification, the "number of carbon atoms" in a functional group means the total number of carbon atoms in the functional group unless otherwise specified. Furthermore, in this specification, for example, a "hydrocarbon group having 1 to 20 carbon atoms" is a general term for hydrocarbon groups having 1, 2, 3, ..., or 20 carbon atoms, and this also has a similar meaning in other functional groups for which the number of carbon atoms is specified, unless otherwise specified.

[0021] R 1 ~R 3In the above formula, examples of the hydrocarbon group having 1 to 20 carbon atoms include alkyl groups having 1 to 20 carbon atoms. Furthermore, the alkyl group having 1 to 20 carbon atoms is not particularly limited, and examples thereof include chain alkyl groups such as methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups, and cyclic alkyl groups such as cyclopentyl and cyclohexyl groups. 1 ~R 3 In the above, the hydrocarbon group having 1 to 20 carbon atoms is preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrocarbon group having 1 to 6 carbon atoms, and particularly preferably a hydrocarbon group having 1 to 3 carbon atoms.

[0022] R 1 ~R 3 The alkoxy group having 1 to 20 carbon atoms in the formula (I) is not particularly limited, and examples thereof include linear alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentoxy, and hexoxy groups, and cyclic alkoxy groups such as cyclopentoxy and cyclohexoxy groups. 1 ~R 3 In the above, the alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 10 carbon atoms, more preferably an alkoxy group having 1 to 6 carbon atoms, and particularly preferably an alkoxy group having 1 to 3 carbon atoms.

[0023] R 1 ~R 3 In the above, the hydrocarbon group having 1 to 20 carbon atoms and a halogen atom means a functional group in which some or all of the hydrogen atoms in the hydrocarbon group have been substituted with halogen atoms. The halogen atoms represent fluorine, chlorine, bromine, and iodine atoms. 1 ~R 3 In the above, the hydrocarbon group having 1 to 20 carbon atoms and containing a halogen atom is preferably a hydrocarbon group having 1 to 10 carbon atoms and containing a halogen atom, more preferably a hydrocarbon group having 1 to 6 carbon atoms and containing a halogen atom, and particularly preferably a hydrocarbon group having 1 to 3 carbon atoms and containing a halogen atom.

[0024] R 1 ~R 3 In the above, the hydrocarbon group having 1 to 20 carbon atoms and a heteroatom refers to a functional group in which some or all of the hydrogen atoms and / or some of the carbon atoms in the hydrocarbon group are substituted with heteroatoms. The heteroatoms represent atoms such as oxygen, nitrogen, sulfur, and phosphorus. 1 ~R 3 In the above, the hydrocarbon group having a heteroatom and a carbon number of 1 to 20 is preferably a hydrocarbon group having a heteroatom and a carbon number of 1 to 10, more preferably a hydrocarbon group having a heteroatom and a carbon number of 1 to 6, and particularly preferably a hydrocarbon group having a heteroatom and a carbon number of 1 to 3.

[0025] R 1 ~R 3The hydrocarbon group having a halogen atom or a hetero atom in the formula (I) is not particularly limited, and examples thereof include an iodomethyl group, a bromomethyl group, a chloromethyl group, a fluoromethyl group, a diiodomethyl group, a dibromomethyl group, a dichloromethyl group, a difluoromethyl group, a triiodomethyl group, a tribromomethyl group, a trichloromethyl group, a trifluoromethyl group, a 2-iodoethyl group, a 2-bromoethyl group, a 2-chloroethyl group, a 2-fluoroethyl group, a 1,2-diiodoethyl group, a 1,2-dibromo ... chain halogenated alkyl groups such as 2,2-dichloroethyl group, 1,2-difluoroethyl group, 2,2-diiodoethyl group, 2,2-dibromoethyl group, 2,2-dichloroethyl group, 2,2-difluoroethyl group, 2,2,2-tribromoethyl group, 2,2,2-trichloroethyl group, 2,2,2-trifluoroethyl group, and hexafluoro-2-propyl group; cyclic halogenated alkyl groups such as 2-iodocyclohexyl group, 2-bromocyclohexyl group, 2-chlorocyclohexyl group, and 2-fluorocyclohexyl group; heteroalkyl groups such as 2-iodophenyl, 2-bromophenyl, 2-chlorophenyl, 2-fluorophenyl, 3-iodophenyl, 3-bromophenyl, 3-chlorophenyl, 3-fluorophenyl, 4-iodophenyl, 4-bromophenyl, 4-chlorophenyl, 4-iodophenyl, 4-bromophenyl, 4-chlorophenyl, 4- Halogenated aryl groups such as fluorophenyl group, 2,6-diiodophenyl group, 2,6-dibromophenyl group, 2,6-dichlorophenyl group, 2,6-difluorophenyl group, 3,5-diiodophenyl group, 3,5-dibromophenyl group, 3,5-dichlorophenyl group, 3,5-difluorophenyl group, pentaiodophenyl group, pentabromophenyl group, pentachlorophenyl group, and pentafluorophenyl group; 2-nitrophenyl group, 4-nitrophenyl group, 2,4-dinitrophenyl group;Examples include heteroaryl groups such as a 6-dinitrophenyl group and a 3-amino-2-naphthyl group, halogen-containing heteroalkyl groups such as 2-fluorophosphonooxyethyl, 2-difluorophosphoryloxyethyl, 2-fluorosulfonyloxyethyl, 3-fluorophosphonooxypropyl, 3-difluorophosphoryloxypropyl, 3-fluorosulfonyloxypropyl, 4-fluorophosphonooxybutyl, 4-difluorophosphoryloxybutyl, and 4-fluorosulfonyloxybutyl, and halogen-containing heteroaryl groups such as 4-fluorophosphonooxyphenyl, 4-difluorophosphoryloxyphenyl, and 4-fluorosulfonyloxyphenyl.

[0026] R 1 ~R 3 In the above, the hydrocarbon group having 1 to 20 carbon atoms and an unsaturated bond refers to, for example, a hydrocarbon group having 1 to 20 carbon atoms and a double bond or triple bond between carbon atoms. Furthermore, the hydrocarbon group having an unsaturated bond is preferably a hydrocarbon group having 1 to 10 unsaturated bonds, more preferably a hydrocarbon group having 1 to 5 unsaturated bonds, and particularly preferably a hydrocarbon group having 1 to 3 unsaturated bonds.

[0027] R 1 ~R 3In the above, the hydrocarbon group having 1 to 20 carbon atoms and an unsaturated bond is not particularly limited, and examples thereof include ethenyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-2-propenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, and 3-pentenyl. group, 4-pentenyl group, penta-1,4-dienyl group, penta-2,4-dienyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group, hexa-1,3-dienyl group, hexa-1,5-dienyl group, hexa-2,4-dienyl group, hexa-2,5-dienyl group, hexa-3,5-dienyl group, 3 chain alkenyl groups such as 1-cyclopentenyl, 2-cyclopentenyl, 2,4-cyclopentadienyl, 1-cyclohexenyl, 2-cyclohexenyl, and 3-cyclohexenyl; aryl groups such as phenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,6-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 1-naphthyl, and 2-naphthyl; and chain alkynyl groups such as ethynyl, 2-propynyl, butynyl, 2-butynyl, 3-butynyl, pentynyl, 2-pentynyl, 3-pentynyl, and 4-pentynyl.

[0028] R 1 ~R 3 In the above, the alkoxy group having 1 to 20 carbon atoms and a halogen atom means a functional group in which some or all of the hydrogen atoms in the alkoxy group have been substituted with halogen atoms. Here, the halogen atom means a fluorine, chlorine, bromine, or iodine atom, as in the above case. 1 ~R 3 In the above, the alkoxy group having 1 to 20 carbon atoms and containing a halogen atom is preferably an alkoxy group having 1 to 10 carbon atoms and containing a halogen atom, more preferably an alkoxy group having 1 to 6 carbon atoms and containing a halogen atom, and particularly preferably an alkoxy group having 1 to 3 carbon atoms and containing a halogen atom.

[0029] In addition, the R 1 ~R 3 In the above, the alkoxy group having 1 to 20 carbon atoms and a heteroatom refers to a functional group in which some or all of the hydrogen atoms and / or some of the carbon atoms in the alkoxy group are substituted with heteroatoms. Here, the heteroatom refers to atoms such as oxygen, nitrogen, sulfur, and phosphorus, as in the above case. 1 ~R 3 In the above, the alkoxy group having 1 to 20 carbon atoms and a heteroatom is preferably an alkoxy group having 1 to 10 carbon atoms and a heteroatom, more preferably an alkoxy group having 1 to 6 carbon atoms and a heteroatom, and particularly preferably an alkoxy group having 1 to 3 carbon atoms.

[0030] R 1 ~R 3The alkoxy group having a halogen atom or a hetero atom in the formula (I) is not particularly limited, and examples thereof include an iodomethoxy group, a bromomethoxy group, a chloromethoxy group, a fluoromethoxy group, a diiodomethoxy group, a dibromomethoxy group, a dichloromethoxy group, a difluoromethoxy group, a triiodomethoxy group, a tribromomethoxy group, a trichloromethoxy group, a trifluoromethoxy group, a 2-iodoethoxy group, a 2-bromoethoxy group, a 2-chloroethoxy group, a 2-fluoroethoxy group, a 1,2-diiodoethoxy group, a 1,2-dibromoethoxy group, a 1 chain-containing halogenated alkoxy groups such as 2,2-dichloroethoxy group, 1,2-difluoroethoxy group, 2,2-diiodoethoxy group, 2,2-dibromoethoxy group, 2,2-dichloroethoxy group, 2,2-difluoroethoxy group, 2,2,2-tribromoethoxy group, 2,2,2-trichloroethoxy group, 2,2,2-trifluoroethoxy group, and hexafluoro-2-propoxy group; cyclic-containing halogenated alkoxy groups such as 2-iodocyclohexyloxy group, 2-bromocyclohexyloxy group, 2-chlorocyclohexyloxy group, and 2-fluorocyclohexyloxy group; Halogenated alkoxy groups, heteroalkoxy-containing groups such as 2-methoxyethoxy, 2-(2-methoxyethoxy)ethoxy, 2-(2-(2-methoxyethoxy)ethoxy)ethoxy, and (2-oxo-1,3-dioxolan-4-yl)methoxy, 2-iodophenoxy, 2-bromophenoxy, 2-chlorophenoxy, 2-fluorophenoxy, 3-iodophenoxy, 3-bromophenoxy, 3-chlorophenoxy, 3-fluorophenoxy, 4-iodophenoxy, 4-bromophenoxy, and 4-chlorophenoxy groups halogenated aryl groups such as 4-fluorophenoxy group, 2,6-diiodophenoxy group, 2,6-dibromophenoxy group, 2,6-dichlorophenoxy group, 2,6-difluorophenoxy group, 3,5-diiodophenoxy group, 3,5-dibromophenoxy group, 3,5-dichlorophenoxy group, 3,5-difluorophenoxy group, pentaiodophenoxy group, pentabromophenoxy group, pentachlorophenoxy group, and pentafluorophenoxy group; 2-nitrophenoxy group, 4-nitrophenoxy group, 2,4-dinitrophenoxy group, 2,Examples include heteroaryl-containing groups such as 6-dinitrophenoxy and 3-amino-2-naphthoxy.

[0031] R 1 ~R 3 In the above, the alkoxy group having 1 to 20 carbon atoms and an unsaturated bond refers to, for example, an alkoxy group having a double bond or a triple bond between carbon atoms. Furthermore, the alkoxy group having an unsaturated bond is preferably an alkoxy group having 1 to 10 unsaturated bonds, more preferably an alkoxy group having 1 to 5 unsaturated bonds, and particularly preferably an alkoxy group having 1 to 3 unsaturated bonds.

[0032] R 1 ~R 3In the above, the alkoxy group having 1 to 20 carbon atoms and an unsaturated bond is not particularly limited, and examples thereof include an ethenyloxy group, a 1-propenyloxy group, a 2-propenyloxy group, an isopropenyloxy group, a 2-methyl-2-propenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, a 3-methyl-2-butenyloxy group, a 1-pentenyloxy group, a 2-pentenyloxy group, a 3-pentenyloxy group, a 4-pentenyloxy group, and the like. penta-1,4-dienyloxy group, penta-2,4-dienyloxy group, 1-hexenyloxy group, 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, hexa-1,3-dienyloxy group, hexa-1,5-dienyloxy group, hexa-2,4-dienyloxy group, hexa-2,5-dienyloxy group, hexa-3,5-dienyloxy group, 3-methyloxy group, chain alkenyloxy groups such as 1-cyclopentenyloxy group, 2-cyclopentenyloxy group, 2,4-cyclopentadienyloxy group, 1-cyclohexenyloxy group, 2-cyclohexenyloxy group, and 3-cyclohexenyloxy group; phenoxy group, 2-methylphenoxy group, 3-methylphenoxy group, 4-methylphenoxy group, 2,6-diphenylmethyl- ... Examples thereof include aryloxy groups such as a methylphenoxy group, a 3,5-dimethylphenoxy group, a 2,4,6-trimethylphenoxy group, a 1-naphthoxy group, and a 2-naphthoxy group; and chain alkynyloxy groups such as an ethynyloxy group, a 2-propynyloxy group, a butynyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a pentynyloxy group, a 2-pentynyloxy group, a 3-pentynyloxy group, and a 4-pentynyloxy group.

[0033] R 1 ~R 3 may be the same or different from each other. 1 ~R 3 The functional groups listed above as are merely examples, and the present embodiment is not limited to these.

[0034] In the chemical formula (A), X is a fluorine atom, -Y 1R 4 group or -Y 2 -ZY 3 Represents the H group.

[0035] The -Y in the X 1 R 4 group, and -Y 2 -ZY 3 In the H group, the Y 1 ~Y 3 are each independently an oxygen atom, a sulfur atom, or an imino group (NR 5 )

[0036] The R in the X 4 and the imino group (NR 5 ) in R 5 represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, or an unsaturated bond.

[0037] R 4 , and R 5 The hydrocarbon group having 1 to 20 carbon atoms and the hydrocarbon group having a halogen atom or the like in the above formula (A) are described in detail in the above formula (B). 1 ~R 3 Therefore, the details are omitted here.

[0038] The Y 1 ~Y 3 The imino group (NR 5 ) is not particularly limited, and examples thereof include NH, N(CH3), N(C2H5), N(CH(CH3)2)), N(C6H5), and N(CH2C6H5).

[0039] The Y 1 R 4 The above Y in 1 is an oxygen atom, and the R 4is a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond; 4 The R group in the formula (A) 1 ~R 3 The alkoxy group is the same as the alkoxy group or the alkoxy group having a halogen atom or the like described in 1. Therefore, the details thereof will be omitted.

[0040] The Y 1 R 4 The above Y in 1 is represented by a sulfur atom -SR 4 The group (thio group) is not particularly limited, and examples thereof include a methylthio group, an ethylthio group, an isopropylthio group, a phenylthio group, and a benzylthio group.

[0041] The Y 1 R 4 The above Y in 1 is an imino group (NR 5 ) represented by -NR 4 R 5 The group (amino group) is not particularly limited, and examples thereof include an amino group (NH2), a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, an isopropylamino group, a diisopropylamino group, a phenylamino group, and a diphenylamino group.

[0042] The -Y in the X 2 -ZY 3 In the H group, Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond (hereinafter, sometimes referred to as a "divalent hydrocarbon group having a halogen atom or the like").

[0043] Unless otherwise specified, the "divalent hydrocarbon group" for Z refers to a substituent having a valence of 2, obtained by removing two hydrogen atoms from any one carbon atom to which two or more hydrogen atoms are bonded, or from any two carbon atoms to which one or more hydrogen atoms are bonded, in a hydrocarbon having one or more carbon atoms.

[0044] The divalent hydrocarbon group having 1 to 20 carbon atoms represented by Z is not particularly limited, and examples thereof include a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, an o-phenylene group, an m-phenylene group, a p-phenylene group, a 1,2-naphthylene group, a 1,3-naphthylene group, a 1,4-naphthylene group, and a 1,8-naphthylene group.

[0045] The divalent hydrocarbon group having 1 to 20 carbon atoms and having a halogen atom or the like in Z is not particularly limited, and examples thereof include *-CH2-CH(CH2Cl)-*, *-CH2-CH(CH2(OCH3))-*, *-CH2-CH(CH2(N(CH3)2)-*, *-C2H4-O-C2H4-*, *-CH2-C(=CH2)-CH2-*, *-C Examples of the * include H2-CH(C6H5)-CH2-*, *-CH2-CH(OCH2-C6H5)-CH2-*, *-CH2-CH(NH2)-CH2-*, *-CH2-C(CH2Br)2-CH2-*, *-CH2-C(Br)(NO2)-CH2-*, *-CH2-C(CH3)(NO2)-CH2-*, *-C6H4-C(O)-*, etc. 2 , and Y 3 and the two * and Y 2 , and Y 3 The combination of bonds with can be selected arbitrarily.

[0046] -Y 2 -ZY 3The substituent represented by the H group is not particularly limited, and examples thereof include -O-(CH2)2-OH, -O-(CH2)2-SH, -O-(CH2)2-NH2, -O-(CH2)3-OH, -O-(CH2)3-SH, -O-(CH2)3-NH2, -O-(C6H4)-OH, and -O-(C6H4)-C(O)-OH.

[0047] Specific examples of the difluorophosphate silyl ester in which X in the chemical formula (A) is represented by a fluorine atom include trichlorosilyl difluorophosphate, dichloromethylsilyl difluorophosphate, chlorodimethylsilyl difluorophosphate, dimethylsilyl difluorophosphate, trimethylsilyl difluorophosphate, dimethylvinylsilyl difluorophosphate, dimethylphenylsilyl difluorophosphate, triethylsilyl difluorophosphate, cyclohexyldimethylsilyl difluorophosphate, triisopropylsilyl difluorophosphate, methyldiphenylsilyl difluorophosphate, etc. However, the difluorophosphate silyl ester in which X in the chemical formula (A) is represented by a fluorine atom is not limited to these compound groups.

[0048] In the chemical formula (A), X is -Y 1 R 4Specific examples of the monofluorophosphate silyl ester represented by the group include, for example, methyltrimethylsilyl monofluorophosphate, ethyltrimethylsilyl monofluorophosphate, isopropyltrimethylsilyl monofluorophosphate, butyltrimethylsilyl monofluorophosphate, allyltrimethylsilyl monofluorophosphate, propargyltrimethylsilyl monofluorophosphate, (2,2,2-trifluoroethyl)trimethylsilyl monofluorophosphate, (1,1,1,3,3,3-hexafluoro-2-propyl)trimethylsilyl monofluorophosphate, and monofluoro Examples of suitable phosphates include (2-(2-(2-methoxyethoxy)ethoxy)ethyl)trimethylsilyl phosphate, (2-oxo-1,3-dioxolan-4-yl)methyltrimethylsilyl monofluorophosphate, phenyltrimethylsilyl monofluorophosphate, benzyltrimethylsilyl monofluorophosphate, methylthiotrimethylsilyl monofluorophosphate, ethylthiotrimethylsilyl monofluorophosphate, phenylthiotrimethylsilyl monofluorophosphate, benzylthiotrimethylsilyl monofluorophosphate, and (dimethylamido)trimethylsilyl monofluorophosphate. However, when X in the chemical formula (A) is -Y 1 R 4 The monofluorophosphate silyl ester represented by the group is not limited to these compound groups.

[0049] In the chemical formula (A), X is -Y 2 -ZY 3 Specific examples of the monofluorophosphate silyl ester represented by the H group include (2-hydroxyethyl)trimethylsilyl monofluorophosphate, (3-hydroxypropyl)trimethylsilyl monofluorophosphate, (3-aminopropyl)trimethylsilyl monofluorophosphate, (3-sulfanylpropyl)trimethylsilyl monofluorophosphate, (2-hydroxyphenyl)trimethylsilyl monofluorophosphate, (3-hydroxyphenyl)trimethylsilyl monofluorophosphate, and (2-carboxyphenyl)trimethylsilyl monofluorophosphate. However, when X in the chemical formula (A) is -Y 2 -ZY 3The monofluorophosphate silyl ester represented by the H group is not limited to these compound groups.

[0050] <Compound represented by the above chemical formula (B)> The compound represented by the chemical formula (B) is shown below.

[0051] [ka]

[0052] In the chemical formula (B), M represents a hydrogen atom, an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium.

[0053] The alkali metal is not particularly limited, and examples thereof include Li, Na, K, Rb, and Cs. Among these alkali metals, Li, Na, and K are preferred from the viewpoint of availability, and Li and Na are more preferred from the viewpoint of versatility of monofluorophosphate ester salts.

[0054] The alkaline earth metal is not particularly limited, and examples thereof include Be, Mg, Ca, Sr, and Ba. Among these alkaline earth metals, Mg, Ca, and Ba are preferred from the viewpoints of availability and safety, and Mg is more preferred from the viewpoint of versatility of monofluorophosphate ester salts.

[0055] The transition metal is not particularly limited, and examples thereof include Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Cu, and Zn. Among these transition metals, Ti, Mn, Fe, Co, Ni, and Cu are preferred from the viewpoint of availability.

[0056] The onium is not particularly limited, and examples thereof include primary ammonium, secondary ammonium, tertiary ammonium, quaternary ammonium, quaternary phosphonium, and sulfonium.

[0057] The primary ammonium is not particularly limited, and examples thereof include methylammonium, ethylammonium, propylammonium, and isopropylammonium.

[0058] The secondary ammonium is not particularly limited, and examples thereof include dimethylammonium, diethylammonium, dipropylammonium, dibutylammonium, ethylmethylammonium, methylpropylammonium, butylmethylammonium, butylpropylammonium, and diisopropylammonium.

[0059] The tertiary ammonium is not particularly limited, and examples thereof include trimethylammonium, triethylammonium, tripropylammonium ammonium, tributylammonium, ethyldimethylammonium, diethylmethylammonium, triisopropylammonium, dimethylisopropylammonium, diethylisopropylammonium, dimethylpropylammonium, butyldimethylammonium, 1-methylpyrrolidinium, 1-ethylpyrrolidinium, 1-propylpyrrolidinium, 1-butylpropylpyrrolidinium, 1-methylimidazolium, 1-ethylimidazolium, 1-propylimidazolium, 1-butylimidazolium, pyrazolium, 1-methylpyrazolium, 1-ethylpyrazolium, 1-propylpyrazolium, 1-butylpyrazolium, and pyridinium.

[0060] The quaternary ammonium is not particularly limited, and examples thereof include aliphatic quaternary ammoniums, imidazoliums, pyridiniums, pyrazoliums, and pyridaziniums.

[0061] Furthermore, the aliphatic quaternary ammoniums are not particularly limited, and examples thereof include tetraethylammonium, tetrapropylammonium, tetraisopropylammonium, ethyltrimethylammonium, diethyldimethylammonium, triethylmethylammonium, trimethylpropylammonium, trimethylisopropylammonium, tetrabutylammonium, butyltrimethylammonium, trimethylpentylammonium, hexyltrimethylammonium, 1-methyl-1-propylpyrrolidinium, 1-ethyl-1-methyl-pyrrolidinium, 1-butyl-1-methylpyrrolidinium, 1-ethyl-1-methyl-piperidinium, and 1-butyl-1-methylpiperidinium.

[0062] The imidazoliums are not particularly limited, and examples thereof include 1,3-dimethyl-imidazolium, 1-ethyl-3-methylimidazolium, 1-n-propyl-3-methylimidazolium, 1-n-butyl-3-methylimidazolium, and 1-n-hexyl-3-methylimidazolium.

[0063] The pyridiniums are not particularly limited, and examples thereof include 1-methylpyridinium, 1-ethylpyridinium, and 1-n-propylpyridinium.

[0064] The pyrazoliums are not particularly limited, and examples thereof include 1,2-dimethylpyrazolium, 2-ethyl-1-methylpyrazolium, 2-methyl-1-propylpyrazolium, 2-butyl-1-methylpyrazolium, 1-methylpyrazolium, 3-methylpyrazolium, 4-methylpyrazolium, 4-iodopyrazolium, 4-bromopyrazolium, 4-iodo-3-methylpyrazolium, 4-bromo-3-methylpyrazolium, and 3-trifluoromethylpyrazolium.

[0065] The pyridaziniums are not particularly limited, and examples thereof include 1-methylpyridazinium, 1-ethylpyridazinium, 1-propylpyridazinium, 1-butylpyridazinium, 3-methylpyridazinium, 4-methylpyridazinium, 3-methoxypyridazinium, 3,6-dichloropyridazinium, 3,6-dichloro-4-methylpyridazinium, 3-chloro-6-methylpyridazinium, and 3-chloro-6-methoxypyridazinium.

[0066] Of the oniums exemplified above, tetramethylammonium, tetraethylammonium, triethylmethylammonium, tributylmethylammonium, 1-methyl-1-propylpyrrolidinium, and 1-ethyl-3-methylimidazolium are preferred from the viewpoints of availability and versatility.

[0067] In the chemical formula (B), the R 6 represents a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond. These are the same as the R 1 ~R 3 The hydrocarbon group is the same as the hydrocarbon group or hydrocarbon group having a halogen atom, etc. described in 1. Therefore, the details thereof will be omitted.

[0068] In the chemical formula (B), the Y 4 is an oxygen atom, a sulfur atom, or an imino group (NR 7 )

[0069] The imino group (NR 7 ) is an imino group (NR 5 ) and therefore the details are omitted.

[0070] In the chemical formula (B), n is the valence of the cation and represents a natural number of 1 to 5.

[0071] The Y in the chemical formula (B)4Specific examples of the compound in which M is an oxygen atom and M is a hydrogen atom include chain alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropyl alcohol, pentanol, hexanol, heptanol, and octanol, cyclic alkyl alcohols such as cyclopentanol and cyclohexanol, 2-iodoethanol, 2-bromoethanol, 2-chloroethanol, 2-fluoroethanol, 1,2-diiodoethanol, 1,2-dibromoethanol, 1,2-dichloroethanol, and 1,2-difluoroethanol. Chain halogen-containing fluoroethanol, such as fluoroethanol, 2,2-diiodoethanol, 2,2-dibromoethanol, 2,2-dichloroethanol, 2,2-difluoroethanol, 2,2,2-tribromoethanol, 2,2,2-trichloroethanol, 2,2,2-trifluoroethanol, 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,3-heptafluoro-1-propanol, 1,1,1,3,3,3-hexafluoro-2-propanol, and 4,4,5,5,6,6,7,7,7-nonafluoro-1-heptanol. Alcohols, cyclic halogen-containing alkyl alcohols such as 2-iodocyclohexanol, 2-bromocyclohexanol, 2-chlorocyclohexanol, and 2-fluorocyclohexanol, chain alkenyl alcohols such as allyl alcohol, crotyl alcohol, 3-buten-1-ol, cis-2-penten-1-ol, 1-penten-3-ol, 4-penten-1-ol, and 4-penten-2-ol, cyclic alkenyl alcohols such as 2-cyclohexen-1-ol and 3-cyclohexen-1-ol, propargylic acid, and the like. Chain alkynyl alcohols such as 2-butyn-1-ol, 3-butyn-1-ol, 3-butyn-2-ol, 1-pentyn-3-ol, 2-pentyn-1-ol, 3-pentyn-1-ol, 4-pentyn-1-ol, and 4-pentyn-2-ol, methyl cellosolve, ethyl cellosolve, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, tetraethylene glycol monomethyl ether, 4-hydroxymethyl-2-oxo-1,Heteroalcohols such as 3-dioxolane, halogen-containing heteroalcohols such as 2-fluorophosphonooxyethanol, 2-difluorophosphoryloxyethanol, 2-fluorosulfonyloxyethanol, 3-fluorophosphonooxypropanol, 3-difluorophosphoryloxypropanol, 3-fluorosulfonyloxypropanol, 4-fluorophosphonooxybutanol, 4-difluorophosphoryloxybutanol, and 4-fluorosulfonyloxybutanol, chain diols such as ethylene glycol, propylene glycol, 1,3-butanediol, and triethylene glycol, cyclic diols such as 1,2-cyclohexanediol, 1,3-cyclohexanediol, and 1,4-cyclohexanediol, chain triols such as trimethylolethane and trimethylolpropane, sugar alcohols such as sorbitol, maltitol, xylitol, mannitol, and erythritol, phenol, hydroquinone, phloroglucinol, catechol, resorcinol, pyrogallol, and o-cresol. m-cresol, p-cresol, 2-methoxyphenol, 3-methoxyphenol, 4-methoxyphenol, 5-methoxyresorcinol, 3,5-dimethoxyphenol, 4-phenoxyphenol, 2-aminophenol, 3-aminophenol, 4-aminophenol, 2-cyanophenol, 3-cyanophenol, 4-cyanophenol, 2-ethylphenol, 3-ethylphenol, 4-ethylphenol, 2,3-dimethylphenol, 2,4-dimethylphenol, 2,5-dimethylphenol, 2,6-dimethylphenol, 3,4-dimethylphenol, 5-amino-2-methylphenol, 2-amino-3-methylphenol, 6-amino-3-methylphenol, 4-amino-2-methylphenol, 2-amino-4-methylphenol, 4-amino-3-methylphenol, 3-amino-4-methylphenol, 2-mercaptophenol, 2-allylphenol, 4-allylphenol, 2-acetylphenol, 3-acetylphenol, 4-acetylphenol, 2,4,Phenols such as 6-trimethylphenol, 2-methylthiophenol, 4-methylthiophenol, 3-tert-butylphenol, 2-tert-butylphenol, 4-tert-butylphenol, 3-phenylphenol, 4-phenylphenol, 2-phenylphenol, 4-cyclohexylphenol, 2-cyclohexylphenol, 2-benzylphenol, 4-benzylphenol, 4-(1-adamantyl)phenol, 2-fluorophenol, 3-fluorophenol, 4-fluorophenol, 4-fluoro-3- Methylphenol, 4-fluoro-2-methylphenol, 3-fluoro-4-methylphenol, 5-fluoro-2-methylphenol, 4-chlorophenol, 2-chlorophenol, 3-chlorophenol, 2,6-difluorophenol, 3,5-difluorophenol, 3,4-difluorophenol, 2,4-difluorophenol, 2,3-difluorophenol, 2,5-difluorophenol, 2,3,4-trifluorophenol, 2,3,6-trifluorophenol, 3,4,5-trifluorophenol, 2,3,5,6-tetrafluorophenol Trifluorophenol, pentafluorophenol, 2-trifluoromethylphenol, 4-trifluoromethylphenol, 3-trifluoromethylphenol, 3,5-dichlorophenol, 3,4-dichlorophenol, 2,4-dichlorophenol, 2,5-dichlorophenol, 2,6-dichlorophenol, 4-bromophenol, 3-bromophenol, 2-bromophenol, 3,4,5-trichlorophenol, 2,4,6-trichlorophenol, 3-iodophenol, 2-iodophenol, 4-iodophenol, 3,5 halogen-containing phenols such as 4-dibromophenol, 2,6-dibromophenol, 2,4-dibromophenol, 2,4,6-tribromophenol, and 2,4,6-triiodophenol; halogen-containing heterophenols such as 4-fluorophosphonooxyphenol, 4-difluorophosphoryloxyphenol, and 4-fluorosulfonyloxyphenol; 1-naphthol, 2-naphthol, 1,6-dihydroxynaphthol, 2,7-dihydroxynaphthol, 2,6-dihydroxynaphthol, 1,7-dihydroxynaphthol, 5,6,7,Examples of the naphthols include 8-tetrahydro-2-naphthol, 5,6,7,8-tetrahydro-1-naphthol, 3-amino-2-naphthol, and 5-amino-1-naphthol. These may be used alone or in combination of two or more. However, the above Y in the chemical formula (B) may be used in combination of two or more. 4 The compounds where is an oxygen atom and M is a hydrogen atom are not limited to these compound groups.

[0072] The Y in the chemical formula (B) 4is an oxygen atom, and specific examples of compounds in which M is other than a hydrogen atom include lithium methoxide, sodium methoxide, potassium methoxide, magnesium methoxide, calcium methoxide, zinc methoxide, titanium (IV) methoxide, germanium (IV) methoxide, tantalum (V) methoxide, tetrabutylammonium methoxide, lithium ethoxide, sodium ethoxide, potassium ethoxide, magnesium ethoxide, aluminum ethoxide, antimony (III) ethoxide, and titanium (IV) ethoxide. , germanium(IV) ethoxide, zirconium(IV) ethoxide, tantalum(V) ethoxide, niobium(V) ethoxide, titanium(IV) propoxide, zirconium(IV) propoxide, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, magnesium tert-butoxide, barium tert-butoxide, aluminum tert-butoxide, aluminum sec-butoxide, yttrium(III) butoxide, titanium(IV) tert-butoxide, titanium(IV) butoxide alkoxides such as t-butoxide, zirconium (IV) butoxide, tin (IV) tert-butoxide, hafnium (IV) tert-butoxide, hafnium (IV) butoxide, tantalum (V) butoxide, lithium phenoxide, sodium phenoxide, potassium phenoxide, cesium phenoxide, triethylmethylammonium phenoxide, lithium 2-methylphenoxide, lithium 3-methylphenoxide, lithium 4-methylphenoxide, lithium 2-aminophenoxide, lithium 3-aminophenoxide, lithium Lithium 4-aminophenoxide, Lithium 2-fluorophenoxide, Lithium 3-fluorophenoxide, Lithium 4-fluorophenoxide, Lithium 2-cyanophenoxide, Lithium 3-cyanophenoxide, Lithium 4-cyanophenoxide, Lithium 2-ethylphenoxide, Lithium 3-ethylphenoxide, Lithium 4-ethylphenoxide, Lithium 2,3-dimethylphenoxide, Lithium 2,4-dimethylphenoxide, Lithium 2,5-dimethylphenoxide, Lithium 2,6-dimethylphenoxide, Lithium 3,4-Dimethylphenoxide, Lithium 5-amino-2-methylphenoxide, Lithium 2-amino-3-methylphenoxide, Lithium 6-amino-3-methylphenoxide, Lithium 4-amino-2-methylphenoxide, Lithium 2-amino-4-methylphenoxide, Lithium 4-amino-3-methylphenoxide, Lithium 3-amino-4-methylphenoxide, Lithium 3-methoxyphenoxide, Lithium 2-methoxyphenoxide, Lithium 4-methoxyphenoxide, Lithium 4-fluoro-3-methylphenoxide, Lithium 4 -Fluoro-2-methylphenoxide, Lithium 3-fluoro-4-methylphenoxide, Lithium 5-fluoro-2-methylphenoxide, Lithium 2-mercaptophenoxide, Lithium 4-chlorophenoxide, Lithium 2-chlorophenoxide, Lithium 3-chlorophenoxide, Lithium 2,6-difluorophenoxide, Lithium 3,5-difluorophenoxide, Lithium 3,4-difluorophenoxide, Lithium 2,4-difluorophenoxide, Lithium 2,3-difluorophenoxide, Lithium 2,5-difluorophenoxide Cide, lithium 2,3,4-trifluorophenoxide, lithium 2,3,6-trifluorophenoxide, lithium 3,4,5-trifluorophenoxide, lithium 2,3,5,6-tetrafluorophenoxide, lithium pentafluorophenoxide, lithium 2-allylphenoxide, lithium 4-allylphenoxide, lithium 2-acetylphenoxide, lithium 3-acetylphenoxide, lithium 4-acetylphenoxide, lithium 2,4,6-trimethylphenoxide, lithium 2-methylthiophenoxide, lithium 4-methylphenoxide Lithium thiophenoxide, lithium 2-naphthoxide, lithium 1-naphthoxide, lithium 5,6,7,8-tetrahydro-2-naphthoxide, lithium 5,6,7,8-tetrahydro-1-naphthoxide, lithium 3-tert-butylphenoxide, lithium 2-tert-butylphenoxide, lithium 4-tert-butylphenoxide, lithium 2-trifluoromethylphenoxide, lithium 4-trifluoromethylphenoxide, lithium 3-trifluoromethylphenoxide, lithium 3,5-dichlorophenoxide, lithium 3,4-Dichlorophenoxide, Lithium 2,4-Dichlorophenoxide, Lithium 2,5-Dichlorophenoxide, Lithium 2,6-Dichlorophenoxide, Lithium 3-Phenylphenoxide, Lithium 4-Phenylphenoxide, Lithium 2-Phenylphenoxide, Lithium 4-Bromophenoxide, Lithium 3-Bromophenoxide, Lithium 2-Bromophenoxide, Lithium 4-Cyclohexylphenoxide, Lithium 2-Cyclohexylphenoxide, Lithium 2-Benzylphenoxide, Lithium 4-Benzylphenoxide, Lithium 4-Phenoxyphenoxide oxide, lithium 3,4,5-trichlorophenoxide, lithium 2,4,6-trichlorophenoxide, lithium 3-iodophenoxide, lithium 2-iodophenoxide, lithium 4-iodophenoxide, lithium 4-(1-adamantyl)phenoxide, lithium 3,5-dibromophenoxide, lithium 2,6-dibromophenoxide, lithium 2,4-dibromophenoxide, lithium 2,4,6-tribromophenoxide, lithium 2,4,6-triiodophenoxide, lithium 4-triphenylmethylphenoxide, and other phenoxy compounds. 4 The compounds where is an oxygen atom and where M is other than a hydrogen atom are not limited to these compound groups.

[0073] The Y in the chemical formula (B) 4 Specific examples of compounds in which Y is a sulfur atom and M is a hydrogen atom include ethyl mercaptan, 1-propanethiol, 2-propanethiol, 1-butanethiol, tert-butyl mercaptan, allyl mercaptan, 2-aminoethanethiol, 2-mercaptoethanol, 3-mercapto-1-propanol, 1,2-ethanedithiol, 1,3-propanedithiol, cyclopentanethiol, cyclohexanethiol, benzenethiol, benzyl mercaptan, and thiosalicylic acid. These compounds can be used alone or in combination of two or more. However, the Y in the chemical formula (B) can be used alone or in combination of two or more. 4 The compounds where R is a sulfur atom and M is a hydrogen atom are not limited to these compound groups.

[0074] The Y in the chemical formula (B) 4 Specific examples of the compound in which Y is a sulfur atom and M is other than a hydrogen atom include lithium thioethoxide, sodium thioethoxide, and sodium thiophenoxide. 4 The compounds where is a sulfur atom and where M is other than a hydrogen atom are not limited to these compound groups.

[0075] The Y in the chemical formula (B) 4 is an imino group (NR 7 ) Specific examples of compounds in which M is a hydrogen atom include ammonia, methylamine, dimethylamine, ethylamine, diethylamine, isopropylamine, diisopropylamine, phenylamine, and diphenylamine. These can be used alone or in combination of two or more. However, when the Y in the chemical formula (B) is 4 is an imino group (NR 7 ), the compounds in which M is a hydrogen atom are not limited to these compound groups.

[0076] The Y in the chemical formula (B) 4 is an imino group (NR 7 Specific examples of the compound in which M is other than a hydrogen atom include lithium amide, sodium amide, potassium amide, and lithium diisopropylamide. However, when the Y in the chemical formula (B) is 4 is an imino group (NR 7 ), the compounds in which M is other than a hydrogen atom are not limited to these compound groups.

[0077] <Phosphorus Compounds Produced in Step (I)> The phosphorus compound produced in the step (I) is represented by the following chemical formula (C).

[0078] [ka]

[0079] In the chemical formula (C), the M and Y 4 , R 6 , X, and n are all the same as those in the chemical formulas (A) and (B), and therefore, details thereof will be omitted.

[0080] In the chemical formula (C), X is a fluorine atom, and Y is a 4Specific examples of monofluorophosphate esters in which M is an oxygen atom and M is a hydrogen atom include methyl monofluorophosphate, ethyl monofluorophosphate, propyl monofluorophosphate, isopropyl monofluorophosphate, butyl monofluorophosphate, pentyl monofluorophosphate, hexyl monofluorophosphate, heptyl monofluorophosphate, octyl monofluorophosphate, nonyl monofluorophosphate, decyl monofluorophosphate, cyclohexyl monofluorophosphate, and (2,2,2-trifluoroethylene) monofluorophosphate. ethyl), 2,2,3,3-tetrafluoro-1-propyl monofluorophosphate, 1,1,1,3,3,3-hexafluoro-2-propyl monofluorophosphate, 2-fluorocyclohexyl monofluorophosphate, allyl monofluorophosphate, 2-cyclohexen-1-yl monofluorophosphate, propargyl monofluorophosphate, 2-(2-(2-methoxyethoxy)ethoxy)ethyl monofluorophosphate, 2-oxo-1,3-dioxolan-4-yl)methyl monofluorophosphate, monofluorophosphate Examples of suitable fluorophosphates include 2-hydroxyethyl monofluorophosphate, 3-hydroxypropyl monofluorophosphate, 2-fluorophosphonooxyethyl monofluorophosphate, 2-difluorophosphoryloxyethyl monofluorophosphate, 2-fluorosulfonyloxyethyl monofluorophosphate, 3-fluorophosphonooxypropyl monofluorophosphate, 3-difluorophosphoryloxypropyl monofluorophosphate, 3-fluorosulfonyloxypropyl monofluorophosphate, 4-fluorophosphonooxybutyl monofluorophosphate, 4-difluorophosphoryloxybutyl monofluorophosphate, 4-fluorosulfonyloxybutyl monofluorophosphate, phenyl monofluorophosphate, 4-fluorophenyl monofluorophosphate, pentafluorophenyl monofluorophosphate, 4-fluorophosphonooxyphenyl monofluorophosphate, 4-difluorophosphoryloxyphenyl monofluorophosphate, 4-fluorosulfonyloxyphenyl monofluorophosphate, and 1-naphthyl monofluorophosphate. However, in the case where X in the chemical formula (C) is a fluorine atom and Y 4The monofluorophosphate esters in which is an oxygen atom and the M is a hydrogen atom are not limited to these compound groups.

[0081] In the chemical formula (C), X is a fluorine atom, and Y is a 4Specific examples of the monofluorophosphate ester salts where M is an oxygen atom and M is other than a hydrogen atom include lithium methyl monofluorophosphate, sodium methyl monofluorophosphate, potassium methyl monofluorophosphate, magnesium methyl monofluorophosphate, calcium methyl monofluorophosphate, aluminum methyl monofluorophosphate, tetrabutylammonium methyl monofluorophosphate, lithium ethyl monofluorophosphate, sodium ethyl monofluorophosphate, potassium ethyl monofluorophosphate, magnesium ethyl monofluorophosphate, calcium ethyl monofluorophosphate, aluminum ethyl monofluorophosphate, tetrabutylammonium ethyl monofluorophosphate, lithium (tert-butyl) monofluorophosphate, sodium (tert-butyl) monofluorophosphate, potassium (tert-butyl) monofluorophosphate, magnesium (tert-butyl) monofluorophosphate, calcium (tert-butyl) monofluorophosphate, aluminum (tert-butyl) monofluorophosphate, tetrabutylammonium monofluorophosphate, and lithium phenyl monofluorophosphate, sodium phenyl monofluorophosphate, potassium phenyl monofluorophosphate, triethylmethylammonium phenyl monofluorophosphate, methyltin monofluorophosphate, copper methyl monofluorophosphate, silver monofluorophosphate, tetramethylammonium methyl monofluorophosphate, tetraethylammonium methyl monofluorophosphate, triethylmethylammonium methyl monofluorophosphate, tributylmethylammonium methyl monofluorophosphate, 1-methyl-1-propylpyrrolidinium methyl monofluorophosphate, 1-ethyl-3-methylimidazolium methyl monofluorophosphate, tin monofluorophosphate, copper ethyl monofluorophosphate, silver monofluorophosphate, tetramethylammonium ethyl monofluorophosphate, tetraethylammonium ethyl monofluorophosphate, triethylmethylammonium ethyl monofluorophosphate, tributylmethylammonium ethyl monofluorophosphate, 1-methyl-1-propylpyrrolidinium ethyl monofluorophosphate, 1-ethyl-3-methylimidazolium ethyl monofluorophosphate,Isopropyl lithium monofluorophosphate, isopropyl sodium monofluorophosphate, potassium isopropyl magnesium monofluorophosphate, isopropyl calcium monofluorophosphate, isopropyl aluminum monofluorophosphate, isopropyl tin monofluorophosphate, isopropyl copper monofluorophosphate, isopropyl silver monofluorophosphate, isopropyl tetramethylammonium monofluorophosphate, isopropyl tetraethylammonium monofluorophosphate, isopropyl triethylmethylammonium monofluorophosphate, isopropyl tributylmethylammonium monofluorophosphate, isopropyl 1-methyl-1-propylpyrrolidinium monofluorophosphate, isopropyl 1-ethyl-3-methylimidazolium monofluorophosphate, butyllithium monofluorophosphate, sodium butyl monofluorophosphate, potassium butyl monofluorophosphate, butyl magnesium monofluorophosphate, butyl calcium monofluorophosphate, butyl aluminum monofluorophosphate, butyl tin monofluorophosphate, butyl copper monofluorophosphate , butyl silver monofluorophosphate, butyl tetramethylammonium monofluorophosphate, butyl tetraethylammonium monofluorophosphate, butyl triethylmethylammonium monofluorophosphate, butyl tributylmethylammonium monofluorophosphate, butyl 1-methyl-1-propylpyrrolidinium monofluorophosphate, butyl 1-ethyl-3-methylimidazolium monofluorophosphate, lithium allyl monofluorophosphate, sodium allyl monofluorophosphate, potassium allyl monofluorophosphate, magnesium allyl monofluorophosphate, calcium allyl monofluorophosphate, allyl aluminum monofluorophosphate, allyl tin monofluorophosphate, copper allyl monofluorophosphate, allyl silver monofluorophosphate, allyl tetramethylammonium monofluorophosphate, allyl tetraethylammonium monofluorophosphate, allyl triethylmethylammonium monofluorophosphate, allyl tributylmethylammonium monofluorophosphate, allyl 1-methyl-1-propylpyrrolidinium monofluorophosphate, allyl 1-ethyl-3-methylimidazolium monofluorophosphate,Lithium propargyl monofluorophosphate, Sodium propargyl monofluorophosphate, Potassium propargyl monofluorophosphate, Magnesium propargyl monofluorophosphate, Calcium propargyl monofluorophosphate, Aluminum propargyl monofluorophosphate, Tin propargyl monofluorophosphate, Copper propargyl monofluorophosphate, Silver propargyl monofluorophosphate, Tetramethylammonium propargyl monofluorophosphate, Tetraethylammonium propargyl monofluorophosphate, Triethylmethylammonium propargyl monofluorophosphate, Tributylmethylammonium propargyl monofluorophosphate, 1-methyl-1-propylpyrrolidinium propargyl monofluorophosphate, 1-ethyl-3-methylimidazolium propargyl monofluorophosphate, Lithium (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, Sodium (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, Potassium (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, Monofluoro Magnesium (2-(2-(2-methoxyethoxy)ethoxy)ethyl) phosphate, calcium (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, aluminum (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, tin (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, copper (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, silver (2-(2-(2-methoxyethoxy)ethoxy)ethyl) monofluorophosphate, monofluorophosphate (2-(2-(2-methoxyethoxy)ethoxy)ethyl)tetramethylammonium, (2-(2-(2-methoxyethoxy)ethoxy)ethyl)tetraethylammonium monofluorophosphate, (2-(2-(2-methoxyethoxy)ethoxy)ethyl)triethylmethylammonium monofluorophosphate, (2-(2-(2-methoxyethoxy)ethoxy)ethyl)tributylmethylammonium monofluorophosphate, (2-(2-(2-methoxyethoxy)ethoxy)ethyl)1-methyl-1-propylpyrrolidinium monofluorophosphate,1-ethyl-3-methylimidazolium monofluorophosphate (2-(2-(2-methoxyethoxy)ethoxy)ethyl) methyl) monofluorophosphate, lithium monofluorophosphate (2-oxo-1,3-dioxolan-4-yl), sodium monofluorophosphate (2-oxo-1,3-dioxolan-4-yl), potassium monofluorophosphate (2-oxo-1,3-dioxolan-4-yl), magnesium monofluorophosphate (2-oxo-1,3-dioxolan-4-yl), (2-oxo-1,3-dioxolan-4-yl)methyl calcium monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl aluminum monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl tin monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl copper monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl silver monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl tetramethylammonium monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl tetrafluorophosphate Triethylammonium, (2-oxo-1,3-dioxolan-4-yl)methyl triethylmethylammonium monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl tributylmethylammonium monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl 1-methyl-1-propylpyrrolidinium monofluorophosphate, (2-oxo-1,3-dioxolan-4-yl)methyl 1-ethyl-3-methylimidazolium monofluorophosphate, (2,2,2-trifluoroethyl)lithium monofluorophosphate ammonium, monofluorophosphate (2,2,2-trifluoroethyl) sodium, monofluorophosphate (2,2,2-trifluoroethyl) potassium, monofluorophosphate (2,2,2-trifluoroethyl) magnesium, monofluorophosphate (2,2,2-trifluoroethyl) calcium, monofluorophosphate (2,2,2-trifluoroethyl) aluminum, monofluorophosphate (2,2,2-trifluoroethyl) tin, monofluorophosphate (2,2,2-trifluoroethyl) copper, monofluorophosphate (2,2,2-trifluoroethyl) silver,(2,2,2-trifluoroethyl) tetramethylammonium monofluorophosphate, (2,2,2-trifluoroethyl) tetraethylammonium monofluorophosphate, (2,2,2-trifluoroethyl) triethylmethylammonium monofluorophosphate, (2,2,2-trifluoroethyl) tributylmethylammonium monofluorophosphate, (2,2,2-trifluoroethyl) 1-methyl-1-propylpyrrolidinium monofluorophosphate, (2,2,2-trifluoroethyl) 1-ethyl-3-methyl monofluorophosphate Imidazolium, lithium monofluorophosphate (2,2,3,3-tetrafluoro-1-propyl), sodium monofluorophosphate (2,2,3,3-tetrafluoro-1-propyl), potassium monofluorophosphate (2,2,3,3-tetrafluoro-1-propyl), magnesium monofluorophosphate (2,2,3,3-tetrafluoro-1-propyl), calcium monofluorophosphate (2,2,3,3-tetrafluoro-1-propyl), aluminum monofluorophosphate (2,2,3,3-tetrafluoro-1-propyl). , (2,2,3,3-tetrafluoro-1-propyl)tin monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)copper monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)silver monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)tetramethylammonium monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)tetraethylammonium monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)triethylmethylammonium monofluorophosphate monium, (2,2,3,3-tetrafluoro-1-propyl)tributylmethylammonium monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)1-methyl-1-propylpyrrolidinium monofluorophosphate, (2,2,3,3-tetrafluoro-1-propyl)1-ethyl-3-methylimidazolium monofluorophosphate, (1,1,1,3,3,3-hexafluoro-2-propyl)lithium monofluorophosphate, (1,1,1,3,3,3-hexafluoro-2-propyl)sodium monofluorophosphate,Potassium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) phosphate, magnesium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) phosphate, calcium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) phosphate, ,1,1,3,3,3-Hexafluoro-2-propyl)aluminum, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)tin, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)copper, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)silver, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)tetramethylammonium, monofluorophosphate (1,1,1 ,3,3,3-Hexafluoro-2-propyl)tetraethylammonium, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)triethylmethylammonium, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)tributylmethylammonium, monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)1-methyl-1-propylpyrrolidinium, monofluorophosphate (1,1,1,3,3,3-Hexafluoro-2-propyl)1-ethyl-3-methylimidazolium, phenyl magnesium monofluorophosphate, phenyl calcium monofluorophosphate, phenyl aluminum monofluorophosphate, phenyl tin monofluorophosphate, phenyl copper monofluorophosphate, phenyl silver monofluorophosphate, phenyl tetramethylammonium monofluorophosphate, phenyl tetraethylammonium monofluorophosphate, phenyl tributylmethylammonium monofluorophosphate, phenyl 1-methyl-1-propylpyrrolidinium monofluorophosphate, phenyl 1-ethyl-3-methylimidazolium monofluorophosphate, (4-fluorophenyl) lithium monofluorophosphate, (4-fluorophenyl) sodium monofluorophosphate, (4-fluorophenyl) potassium monofluorophosphate, monofluorophosphate Examples of suitable phosphates include (4-fluorophenyl) magnesium monofluorophosphate, (4-fluorophenyl) calcium monofluorophosphate, (4-fluorophenyl) aluminum monofluorophosphate, (4-fluorophenyl) tin monofluorophosphate, (4-fluorophenyl) copper monofluorophosphate, (4-fluorophenyl) silver monofluorophosphate, (4-fluorophenyl) tetramethylammonium monofluorophosphate, (4-fluorophenyl) tetraethylammonium monofluorophosphate, (4-fluorophenyl) triethylmethylammonium monofluorophosphate, (4-fluorophenyl) tributylmethylammonium monofluorophosphate, (4-fluorophenyl) 1-methyl-1-propylpyrrolidinium monofluorophosphate, and (4-fluorophenyl) 1-ethyl-3-methylimidazolium monofluorophosphate, provided that in the chemical formula (C), X is a fluorine atom, Y, 4 The monofluorophosphate salts in which is an oxygen atom and the M is other than a hydrogen atom are not limited to these compound groups.

[0082] In the chemical formula (C), X is a fluorine atom, and Y is a 4Specific examples of the monofluorophosphate thioester in which X is a sulfur atom and M is a hydrogen atom include ethylthio monofluorophosphate, propylthio monofluorophosphate, isopropylthio monofluorophosphate, butylthio monofluorophosphate, cyclohexylthio monofluorophosphate, allylthio monofluorophosphate, 2-hydroxyethylthio monofluorophosphate, 2-aminoethylthio monofluorophosphate, 2-sulfanylethylthio monofluorophosphate, 3-hydroxypropylthio monofluorophosphate, 3-sulfanylpropylthio monofluorophosphate, phenylthio monofluorophosphate, benzylthio monofluorophosphate, etc. However, the monofluorophosphate ester in which X is a fluorine atom, Y4 is a sulfur atom, and M is a hydrogen atom in the chemical formula (C) is not limited to these compound groups.

[0083] In the chemical formula (C), X is a fluorine atom, and Y is a 4 Specific examples of the monofluorophosphate thioester salt in which X is a sulfur atom and M is other than a hydrogen atom include ethylthiolithium monofluorophosphate, ethylthiosodium monofluorophosphate, phenylthiosodium monofluorophosphate, ethylthiopotassium monofluorophosphate, ethylthiomagnesium monofluorophosphate, ethylthiocalcium monofluorophosphate, ethylthioaluminum monofluorophosphate, ethylthiocopper monofluorophosphate, ethylthiosilver monofluorophosphate, ethylthiotin monofluorophosphate, ethylthiotetramethylammonium monofluorophosphate, ethylthio1-ethyl-3-methylimidazolium monofluorophosphate, propylthiolithium monofluorophosphate, isopropylthiolithium monofluorophosphate, butylthiolithium monofluorophosphate, cyclohexylthiolithium monofluorophosphate, allylthiolithium monofluorophosphate, phenylthiolithium monofluorophosphate, and benzylthiolithium monofluorophosphate, provided that in the chemical formula (C), X is a fluorine atom and Y is a fluorine atom. 4The monofluorophosphate thioester salts in which is a sulfur atom and the M is other than a hydrogen atom are not limited to these compound groups.

[0084] In the chemical formula (C), X is a fluorine atom, and Y is a 4 is an imino group (NR 7 ) and specific examples of the monofluoroamidophosphoric acid in which M is a hydrogen atom include monofluorophosphoric acid amide, monofluorodimethylamidophosphoric acid, monofluorodiisopropylamidophosphoric acid, monofluorodiphenylamidophosphoric acid, etc. However, in the chemical formula (C), when X is a fluorine atom and Y is a 4 is an imino group (NR 7 ), the monofluoroamidophosphates in which M is a hydrogen atom are not limited to these compound groups.

[0085] In the chemical formula (C), X is a fluorine atom, and Y is a 4 is an imino group (NR 7 ), specific examples of the monofluoroamidophosphate salt in which M is other than a hydrogen atom include lithium monofluoroamidophosphate, sodium monofluoroamidophosphate, potassium monofluoroamidophosphate, lithium monofluorodiisopropylamidophosphate, lithium monofluorodimethylamidophosphate, sodium monofluorodimethylamidophosphate, potassium monofluorodimethylamidophosphate, magnesium monofluorodimethylamidophosphate, calcium monofluorodimethylamidophosphate, aluminum monofluorodimethylamidophosphate, copper monofluorodimethylamidophosphate, silver monofluorodimethylamidophosphate, tin monofluorodimethylamidophosphate, tetramethylammonium monofluorodimethylamidophosphate, 1-ethyl-3-methylimidazolium monofluorodimethylamidophosphate, and lithium monofluorodiphenylamidophosphate. However, when X is a fluorine atom and Y is a fluorine atom, the following may be mentioned: 4 is an imino group (NR 7 ), the monofluoroamidophosphates in which M is other than a hydrogen atom are not limited to these compound groups.

[0086] In the chemical formula (C), X is -OR 4 group, the Y 4 Specific examples of the phosphate diester in which M is an oxygen atom and M is a hydrogen atom include dimethyl phosphate, diethyl phosphate, diisopropyl phosphate, dibutyl phosphate, diallyl phosphate, dipropargyl phosphate, diphenyl phosphate, di(2,2,2-trifluoroethyl) phosphate, di(2,2,3,3-tetrafluoro-1-propyl) phosphate, di(1,1,1,3,3,3-hexafluoro-2-propyl) phosphate, ethyl methyl phosphate, ethyl isopropyl phosphate, butyl methyl phosphate, and phosphate. butyl ethyl, ethyl (2,2,2-trifluoroethyl) phosphate, ethyl (2,2,3,3-tetrafluoro-1-propyl) phosphate, ethyl (1,1,1,3,3,3-hexafluoro-2-propyl) phosphate, allyl ethyl phosphate, ethyl propargyl phosphate, ethyl (2-(2-(2-methoxyethoxy)ethoxy)ethyl) phosphate, ethyl phenyl phosphate, ethyl (4-fluorophenyl) phosphate, ethyl pentafluorophenyl phosphate, ethyl (1-naphthyl) phosphate, etc. However, in the above chemical formula (C), when X is -OR 4 group, the Y 4 The phosphate diesters in which is an oxygen atom and the M is a hydrogen atom are not limited to these compound groups.

[0087] In the chemical formula (C), X is -OR 4 group, the Y 4Specific examples of the phosphate diester salts where M is an oxygen atom and M is other than a hydrogen atom include dimethyllithium phosphate, diethyllithium phosphate, diphenyllithium phosphate, ethylmethyllithium phosphate, ethylmethylsodium phosphate, potassium ethylmethylmagnesium phosphate, ethylmethylcalcium phosphate, ethylmethylaluminum phosphate, ethylmethyltetrabutylammonium phosphate, ethyl(2,2,2-trifluoroethyl)lithium phosphate, ethyl(2,2,2-trifluoroethyl)sodium phosphate, ethyl(2,2,2-trifluoroethyl)potassium phosphate, ethyl(2,2,2-trifluoroethyl)magnesium phosphate, ethyl(2,2,2-trifluoroethyl)calcium phosphate, ethyl(2,2,2-trifluoroethyl)aluminum phosphate, ethyl(2,2,2-trifluoroethyl)tetrabutylammonium phosphate, ethylphenyllithium phosphate, ethylphenylsodium phosphate, ethylphenylphosphate, ethylphosphate Potassium ethylphenyl, ethylphenyltriethylmethylammonium phosphate, diisopropyllithium phosphate, dibutyllithium phosphate, diallyllithium phosphate, dipropargyllithium phosphate, di(2,2,2-trifluoroethyl)lithium phosphate, di(2,2,3,3-tetrafluoro-1-propyl)lithium phosphate, di(1,1,1,3,3,3-hexafluoro-2-propyl)lithium phosphate, ethylisopropyllithium phosphate, butylmethyllithium phosphate, butylethyllithium phosphate, ethyl(2,2,2-trifluoroethyl)copper phosphate, ethyl(2,2,2-trifluoroethyl)silver phosphate, ethyl(2,2,2-trifluoroethyl)tin phosphate, ethyl(2,2,2-trifluoroethyl)tetramethylammonium phosphate, ethyl(2,2,2-trifluoroethyl)1-ethyl-3-methylimidazolium phosphate, ethyl(2,2,3,3-tetrafluoro-1-propyl)lithium phosphate, ethyl(1,1,1,3,3,3-hexafluoro-2-propyl)lithium, allylethyl lithium phosphate, ethylpropargyl lithium phosphate, ethyl(2-(2-(2-methoxyethoxy)ethoxy)ethyl)lithium phosphate, ethyl(4-fluorophenyl)lithium phosphate, ethylpentafluorophenyl lithium phosphate, ethyl(1-naphthyl)lithium phosphate, etc., provided that in the chemical formula (C), X is -OR, 4 group, the Y 4 The phosphate diester salts in which is an oxygen atom and the M is other than a hydrogen atom are not limited to these compound groups.

[0088] In the chemical formula (C), X is -OR 4 group, the Y 4 Specific examples of the phosphate thioester in which X is a sulfur atom and M is a hydrogen atom include ethyl ethyl thio phosphate, ethyl propyl thio phosphate, ethyl isopropyl thio phosphate, allyl thioethyl phosphate, and ethyl phenyl thio phosphate. However, when X in the chemical formula (C) is -OR 4 group, the Y 4 The phosphoric acid thioester in which is a sulfur atom and the M is a hydrogen atom is not limited to these compound groups.

[0089] In the chemical formula (C), X is -OR 4 group, the Y 4Specific examples of the phosphoric acid thioester salt in which X is a sulfur atom and M is other than a hydrogen atom include ethyl ethylthiolithium phosphate, ethyl ethylthiosodium phosphate, ethyl phenylthiosodium phosphate, ethyl propylthiolithium phosphate, ethyl ethylthiopotassium phosphate, ethyl ethylthiomagnesium phosphate, ethyl ethylthiocalcium phosphate, ethyl ethylthioaluminum phosphate, ethyl ethylthiocopper phosphate, ethyl ethylthiosilver phosphate, ethyl ethylthiotin phosphate, ethyl ethylthiotetramethylammonium phosphate, ethyl ethylthio1-ethyl-3-methylimidazolium phosphate, ethyl propylthiolithium phosphate, ethyl isopropylthiolithium phosphate, allylthioethyllithium phosphate, and ethyl phenylthiolithium phosphate. However, when X in the chemical formula (C) is -OR, 4 group, the Y 4 The phosphoric acid thioester salts in which is a sulfur atom and the M is other than a hydrogen atom are not limited to these compound groups.

[0090] In the chemical formula (C), X is -OR 4 group, the Y 4 is an imino group (NR 7 Specific examples of the amide phosphate ester in which M is a hydrogen atom include ethyl amide phosphate, dimethyl ethyl amide phosphate, diisopropyl ethyl amide phosphate, and diphenyl ethyl amide phosphate. However, when X in the chemical formula (C) is -OR 4 group, the Y 4 is an imino group (NR 7 ), the amide phosphoric acid esters in which M is a hydrogen atom are not limited to these compound groups.

[0091] In the chemical formula (C), X is -OR 4 group, the Y 4 is an imino group (NR 7), specific examples of the amide phosphate ester salt in which M is other than a hydrogen atom include lithium ethyl amide phosphate, sodium ethyl amide phosphate, potassium ethyl amide phosphate, lithium diisopropyl ethyl amide phosphate, lithium ethyl dimethyl amide phosphate, sodium ethyl dimethyl amide phosphate, potassium ethyl dimethyl amide phosphate, magnesium ethyl dimethyl amide phosphate, calcium ethyl dimethyl amide phosphate, aluminum ethyl dimethyl amide phosphate, copper ethyl dimethyl amide phosphate, silver ethyl dimethyl amide phosphate, tin ethyl dimethyl amide phosphate, tetramethylammonium ethyl dimethyl amide phosphate, 1-ethyl-3-methylimidazolium ethyl dimethyl amide phosphate, lithium ethyl diisopropyl amide phosphate, and lithium ethyl diphenyl amide phosphate. However, when X in the chemical formula (C) is not -OR, 4 group, the Y 4 is an imino group (NR 7 ), the amide phosphoric acid ester salts in which M is other than a hydrogen atom are not limited to these compound groups.

[0092] In the chemical formula (C), X is -SR 4 group, the Y 4 Specific examples of the phosphate dithioester in which X is a sulfur atom and M is a hydrogen atom include diethylthio phosphate, diisopropylthio phosphate, diallylthio phosphate, diphenylthio phosphate, allylthioethylthio phosphate, and ethylthiophenylthio phosphate. However, when X in the chemical formula (C) is -SR 4 group, the Y 4 The phosphoric acid dithioester in which is a sulfur atom and the M is a hydrogen atom is not limited to these compound groups.

[0093] In the chemical formula (C), X is -SR 4 group, the Y 4Specific examples of the phosphoric acid dithioester salts in which X is a sulfur atom and M is other than a hydrogen atom include diethylthiolithium phosphate, diethylthiosodium phosphate, diphenylthiosodium phosphate, ethylthiophenylthiosodium phosphate, diisopropylthiolithium phosphate, diallylthiolithium phosphate, diphenylthiolithium phosphate, allylthioethylthiolithium phosphate, ethylthiophenylthiolithium phosphate, ethylthiophenylthiopotassium phosphate, ethylthiophenylthiomagnesium phosphate, ethylthiophenylthiocalcium phosphate, ethylthiophenylthioaluminum phosphate, ethylthiophenylthiocopper phosphate, ethylthiophenylthiosilver phosphate, ethylthiophenylthiotin phosphate, ethylthiophenylthiotetramethylammonium phosphate, and ethylthiophenylthio1-ethyl-3-methylimidazolium phosphate. However, when X in the chemical formula (C) is -SR 4 group, the Y 4 The phosphoric acid dithioester salts in which is a sulfur atom and the M is other than a hydrogen atom are not limited to these compound groups.

[0094] In the chemical formula (C), X is -SR 4 group, the Y 4 is an imino group (NR 7 ), specific examples of the thioamidophosphate ester in which M is a hydrogen atom include phenylthioamidophosphate, dimethylphenylthioamidophosphate, diisopropylphenylthioamidophosphate, and diphenylphenylthioamidophosphate. However, when X in the chemical formula (C) is -SR 4 group, the Y 4 is an imino group (NR 7 ), the amide phosphoric acid thioesters in which M is a hydrogen atom are not limited to these compound groups.

[0095] In the chemical formula (C), X is -SR 4 group, the Y 4 is an imino group (NR 7), specific examples of the amide phosphoric acid thioester salt in which M is other than a hydrogen atom include lithium phenylthioamidophosphate, sodium phenylthioamidophosphate, potassium phenylthioamidophosphate, lithium diisopropyl phenylthioamidophosphate, magnesium phenylthioamidophosphate, calcium phenylthioamidophosphate, aluminum phenylthioamidophosphate, copper phenylthioamidophosphate, silver phenylthioamidophosphate, tin phenylthioamidophosphate, tetramethylammonium phenylthioamidophosphate, 1-ethyl-3-methylimidazolium phenylthioamidophosphate, lithium dimethyl phenylthioamidophosphate, lithium diisopropyl phenylthioamidophosphate, lithium diphenyl phenylthioamidophosphate, etc. However, when X in the chemical formula (C) is -SR 4 group, the Y 4 is an imino group (NR 7 ), the amide phosphoric acid thioester salts in which M is other than a hydrogen atom are not limited to these compound groups.

[0096] In the chemical formula (C), X is —NR 4 R 5 group, the Y 4 is an imino group (NR 7 ), specific examples of diamidophosphates in which M is a hydrogen atom include diamidophosphate, bis(dimethylamido)phosphate, bis(diisopropylamido)phosphate, and amido(dimethylamido)phosphate. However, in the case of the chemical formula (C), when X is -NR 4 R 5 group, the Y 4 is an imino group (NR 7 ), the diamide phosphoric acid in which M is a hydrogen atom is not limited to these compound groups.

[0097] In the chemical formula (C), X is —NR 4 R 5 group, the Y 4 is an imino group (NR 7), specific examples of the diamidophosphate salts in which M is other than a hydrogen atom include lithium diamidophosphate, sodium diamidophosphate, potassium diamidophosphate, lithium bis(diisopropylamido)phosphate, lithium amido(dimethylamido)phosphate, magnesium diamidophosphate, calcium diamidophosphate, aluminum diamidophosphate, copper diamidophosphate, silver diamidophosphate, tin diamidophosphate, tetramethylammonium diamidophosphate, 1-ethyl-3-methylimidazolium diamidophosphate, lithium bis(dimethylamido)phosphate, and sodium bis(diisopropylamido)phosphate. However, when X in the chemical formula (C) is -NR 4 R 5 group, the Y 4 is an imino group (NR 7 ), the phosphoric acid diamide salts in which M is other than a hydrogen atom are not limited to these compound groups.

[0098] <Reaction conditions for step (I)> The reaction molar ratio in step (I) is not particularly limited and may be appropriately set depending on the reactants. The reaction molar ratio between the phosphate silyl ester represented by chemical formula (A) and the compound represented by chemical formula (B) is preferably in the range of 0.1 to 2.5 moles of the compound represented by chemical formula (B) per mole of the phosphate silyl ester represented by chemical formula (A), more preferably in the range of 0.3 to 2.0 moles, and particularly preferably in the range of 0.5 to 1.5 moles, from the viewpoints of removing raw material residues and suppressing by-products.

[0099] The reaction initiation temperature in step (I) is not particularly limited as long as the reaction proceeds, and may be appropriately set depending on the reactants. The reaction initiation temperature is preferably in the range of 0°C to 150°C, and from the viewpoint of improving reactivity and suppressing excess energy, more preferably in the range of 25°C to 140°C, even more preferably in the range of 50°C to 135°C, and particularly preferably in the range of 60°C to 130°C.

[0100] The means for adjusting the reaction initiation temperature is not particularly limited. For example, when the reaction initiation temperature is controlled by cooling so that it is within the above temperature range, the reaction vessel into which the phosphate silyl ester represented by the chemical formula (A) and the compound represented by the chemical formula (B) are charged can be placed in an ice bath or the like. When the reaction initiation temperature is controlled by heating so that it is within the above temperature range, the reaction can be controlled by using an oil bath or the like set at a desired temperature.

[0101] The reaction time in step (I) is not particularly limited and may be appropriately set depending on the reactant species. The reaction time is preferably in the range of 0.1 to 48 hours, and from the viewpoint of improving the reaction efficiency and production efficiency, it is preferably in the range of 0.25 to 32 hours, and particularly preferably in the range of 0.5 to 24 hours.

[0102] The reaction in step (I) can be carried out without a solvent or in a non-aqueous solvent. When the reaction in step (I) is carried out without a solvent, the silyl phosphate represented by chemical formula (A) also functions as a reaction solvent.

[0103] The non-aqueous solvent is not particularly limited as long as it does not cause any problems such as reaction with other reactants or products, but it is preferable to use an aprotic organic solvent.

[0104] The aprotic organic solvent is not particularly limited, and examples thereof include nitriles, esters, ketones, ethers, halogenated hydrocarbons, etc. These may be used alone or in combination of two or more.

[0105] The nitriles are not particularly limited and include, for example, acetonitrile, propanenitrile, etc. These may be used alone or in combination of two or more.

[0106] The esters are not particularly limited, and examples thereof include dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, ethylene carbonate, propylene carbonate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate, etc. These may be used alone or in combination of two or more.

[0107] The ketones are not particularly limited and include, for example, acetone, ethyl methyl ketone, isobutyl methyl ketone, cyclohexanone, etc. These may be used alone or in combination of two or more.

[0108] The ethers are not particularly limited and include, for example, diethyl ether, tetrahydrofuran, dioxane, dimethoxyethane, etc. These may be used alone or in combination of two or more.

[0109] The halogenated hydrocarbon is not particularly limited, and examples thereof include dichloromethane, chloroform, 1,1,2,2-tetrachloroethane, chlorobenzene, etc. These may be used alone or in combination of two or more.

[0110] Other examples of non-aqueous solvents include toluene, N,N-dimethylformamide, dimethyl sulfoxide, nitromethane, and nitroethane.

[0111] Of the non-aqueous solvents exemplified above, in the present invention, nitriles, esters, ketones, ethers, halogenated hydrocarbons, and toluene are preferred from the viewpoints of solubility of the reaction substrates and ease of availability.

[0112] The lower limit of the amount of the nonaqueous solvent used is preferably 1 mole or more, more preferably 10 moles or more, per mole of the phosphate silyl ester represented by chemical formula (A). The upper limit of the amount of the nonaqueous solvent used is preferably 10,000 moles or less, more preferably 1,000 moles or less, and particularly preferably 100 moles or less, per mole of the phosphate silyl ester represented by chemical formula (A). By setting the lower limit of the amount of the nonaqueous solvent to 1 mole or more, a decrease in the reactivity between the phosphate silyl ester represented by chemical formula (A) and the compound represented by chemical formula (B) can be prevented, and a decrease in the yield and purity of the phosphorus compound can be suppressed. On the other hand, by setting the upper limit of the amount of the nonaqueous solvent used to 10,000 moles or less, the energy required for distilling off the nonaqueous solvent can be reduced, preventing disadvantages in industrial production.

[0113] The phosphorus compound represented by the chemical formula (C) obtained in the step (I) may be isolated and purified depending on its purity. The method for isolating and purifying the compound is not particularly limited, and known methods can be used. Specific examples include atmospheric distillation, reduced pressure distillation, filtration, filtration, recrystallization, sublimation purification, silica gel column chromatography, preparative thin layer chromatography (PTLC), high performance liquid chromatography (HPLC), and ion chromatography (IC).

[0114] (Process for producing phosphoric acid compound in step (I')) In this embodiment, it is preferable to include a step (I') of intramolecularly reacting a silyl phosphate ester represented by the following chemical formula (A'), as shown in the chemical reaction formula below, thereby efficiently obtaining a phosphoric acid compound having a cyclic structure represented by the following chemical formula (D).

[0115] [ka]

[0116] <Phosphate silyl ester represented by the above chemical formula (A')> The phosphate silyl ester represented by the chemical formula (A') is a phosphate silyl ester represented by the chemical formula (A), wherein X is -Y 2 -ZY 3 H group. Therefore, R 1 ~R 3 and -Y 2 -ZY 3 The details of the H group are the same as those described above and therefore omitted here. As described in Example 24 below, the chemical formula (A') may be obtained by silylating the phosphorus compound represented by the chemical formula (C) produced in step (I) with a silicon compound such as chlorotrimethylsilane.

[0117] <Phosphate Compound Produced in Step (I')> The phosphate compound produced in the step (I') is represented by the following chemical formula (D).

[0118] [ka]

[0119] In the chemical formula (D), the Y 2 , Y 3 , Z are the same as those in the above chemical formula (A'), and therefore, details thereof will be omitted.

[0120] Specific examples of the phosphate compound represented by the chemical formula (D) include 1,3,2-dioxaphospholane-2-hydroxy-2-oxide, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide, 1,3,2-dithiaphospholane-2-hydroxy-2-oxide, 1,3,2-diazaphospholidine-2-hydroxy-2-oxide, 1,3,2-benzodioxaphosphole-2-hydroxy-2-oxide, 4H-1,3,2-benzodioxaphosphorin-4-one-2-hydroxy-2-oxide, etc. However, the phosphate compound represented by the chemical formula (D) is not limited to these compounds.

[0121] <Reaction conditions for step (I')> The step (I') can be carried out by placing the compound represented by the chemical formula (A') under a predetermined temperature condition. The reaction initiation temperature of the step (I') is not particularly limited as long as the reaction proceeds, and may be appropriately set depending on the reactants. The reaction initiation temperature is preferably in the range of 0°C to 150°C, and from the viewpoint of improving reactivity and suppressing excess energy, it is more preferably in the range of 25°C to 140°C, even more preferably in the range of 50°C to 135°C, and particularly preferably in the range of 60°C to 130°C.

[0122] The means for adjusting the reaction initiation temperature is not particularly limited. For example, when the reaction initiation temperature is controlled by cooling so that it falls within the above-mentioned temperature range, the reaction vessel into which the phosphate silyl ester represented by the above-mentioned chemical formula (A') is charged can be placed in an ice bath or the like. When the reaction initiation temperature is controlled by heating so that it falls within the above-mentioned temperature range, the reaction can be controlled by using an oil bath or the like set at a desired temperature.

[0123] The reaction time in step (I') is not particularly limited and may be appropriately set depending on the reactant species. The reaction time is preferably in the range of 0.1 to 48 hours, and from the viewpoint of improving the reaction efficiency and production efficiency, it is preferably in the range of 0.25 to 32 hours, and particularly preferably in the range of 0.5 to 24 hours.

[0124] The reaction in step (I') can be carried out without a solvent or in a non-aqueous solvent. When the reaction in step (I') is carried out without a solvent, the silyl phosphate represented by chemical formula (A') also functions as a reaction solvent.

[0125] The non-aqueous solvent is not particularly limited as long as it does not cause any problems such as reaction with other reactants or products, but it is preferable to use an aprotic organic solvent.

[0126] The aprotic organic solvent is not particularly limited, and examples thereof include nitriles, esters, ketones, ethers, halogenated hydrocarbons, etc. These may be used alone or in combination of two or more.

[0127] The nitriles, esters, ketones, ethers, and halogenated hydrocarbons may be the same as those used in the non-aqueous solvent described in step (I), and therefore, further details thereof will be omitted.

[0128] The lower limit of the amount of the nonaqueous solvent used is preferably 1 mole or more, more preferably 10 moles or more, per mole of the phosphate silyl ester represented by chemical formula (A'). The upper limit of the amount of the nonaqueous solvent used is preferably 10,000 moles or less, more preferably 1,000 moles or less, and particularly preferably 100 moles or less, per mole of the phosphate silyl ester represented by chemical formula (A'). By setting the lower limit of the amount of the nonaqueous solvent to 1 mole or more, a decrease in the reactivity of the phosphate silyl ester represented by chemical formula (A') itself can be prevented, and a decrease in the yield and purity of the phosphoric acid compound represented by chemical formula (D) can be suppressed. On the other hand, by setting the upper limit of the amount of the nonaqueous solvent used to 10,000 moles or less, the energy required for distilling off the nonaqueous solvent can be reduced, preventing disadvantages in industrial production.

[0129] The phosphoric acid compound represented by chemical formula (D) obtained in step (I') may be isolated and purified depending on its purity. The method for isolating and purifying the compound is not particularly limited, and known methods can be used. Specific examples include atmospheric distillation, reduced pressure distillation, filtration, filtration, recrystallization, sublimation purification, silica gel column chromatography, preparative thin-layer chromatography (PTLC), high-performance liquid chromatography (HPLC), and ion chromatography (IC).

[0130] (Method for producing phosphorus compound in step (II)) In this embodiment, as shown in the chemical reaction formula below, it is preferable to include a step (II) of reacting a phosphorus compound represented by the following chemical formula (C') or a phosphorus compound represented by the following chemical formula (D) with a salt consisting of a cation and an anion represented by the following chemical formula (E). This makes it possible to efficiently obtain a phosphorus compound represented by the following chemical formula (F) or chemical formula (G). The phosphorus compounds obtained in the step (I) and / or the step (I') can be used as the phosphorus compounds represented by the chemical formula (C') and the chemical formula (D) in the step (II).

[0131] [ka]

[0132] [ka]

[0133] <Phosphate Compound Represented by Chemical Formula (C')> The phosphate compound represented by the chemical formula (C') is a compound in which M in the chemical formula (C) is a hydrogen atom. 4 , R 6 The details of X are the same as those described above and will be omitted here.

[0134] <Salt consisting of a cation represented by the above chemical formula (E) and an anion> The salt consisting of the cation and anion is represented by the following chemical formula (E).

[0135] [ka]

[0136] In the chemical formula (E), M' represents an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium.

[0137] The alkali metals, alkaline earth metals, aluminum, transition metals, and oniums are the same as those described for M in the chemical formula (B), and therefore, details thereof will be omitted.

[0138] In the chemical formula (E), Q represents a hydroxide, a carbonate, a hydrogen carbonate, an oxide, or a halogen atom.

[0139] The halogen atoms represent fluorine, chlorine, bromine and iodine atoms.

[0140] In the chemical formula (E), n is the valence of the cation and represents a natural number of 1 to 5.

[0141] In the chemical formula (E), m is the valence of the anion and represents a natural number of 1 to 5.

[0142] Specific examples of the hydroxide represented by chemical formula (E) include lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, cesium hydroxide, magnesium hydroxide, calcium hydroxide, strontium hydroxide, barium hydroxide, aluminum hydroxide, manganese hydroxide, iron (II) hydroxide, zinc hydroxide, copper (II) hydroxide, iron (III) hydroxide, ammonia water, tetramethylammonium hydroxide, tetraethylammonium hydroxide, triethylmethylammonium hydroxide, tributylmethylammonium hydroxide, 1-methyl-1-propylpyrrolidinium hydroxide, 1-ethyl-3-methylimidazolium hydroxide, etc. However, the hydroxide represented by chemical formula (E) is not limited to these compound groups.

[0143] Specific examples of the carbonate represented by the chemical formula (E) include lithium carbonate, sodium carbonate, potassium carbonate, rubidium carbonate, cesium carbonate, magnesium carbonate, calcium carbonate, barium carbonate, manganese(II) carbonate, nickel(II) carbonate, iron(II) carbonate, silver(I) carbonate, ammonium carbonate, etc. However, the carbonate represented by the chemical formula (E) is not limited to these compound groups.

[0144] Specific examples of the bicarbonate represented by the chemical formula (E) include sodium bicarbonate, potassium bicarbonate, cesium bicarbonate, calcium bicarbonate, strontium carbonate, ammonium bicarbonate, etc. However, the bicarbonate represented by the chemical formula (E) is not limited to these compound groups.

[0145] Specific examples of the oxide represented by the chemical formula (E) include calcium oxide, magnesium oxide, barium oxide, strontium oxide, nickel (II) oxide, zinc oxide, tin oxide, lead oxide, silver oxide, vanadium (V) oxide, etc. However, the oxide represented by the chemical formula (E) is not limited to these compounds.

[0146] Specific examples of the halide represented by the chemical formula (E) include lithium fluoride, sodium fluoride, potassium fluoride, lithium chloride, sodium chloride, potassium chloride, lithium bromide, sodium bromide, potassium bromide, lithium iodide, sodium iodide, potassium iodide, magnesium chloride, calcium chloride, aluminum chloride, zinc chloride, tin chloride (II), lead chloride (II), copper chloride (II), iron chloride (II), iron chloride (III), platinum chloride (II), manganese chloride (II), cobalt chloride (II), nickel chloride (II), silver fluoride (I), titanium chloride (IV), ammonium chloride, tetramethylammonium chloride, tetraethylammonium chloride, triethylmethylammonium chloride, tributylmethylammonium bromide, 1-methyl-1-propylpyrrolidinium bromide, 1-ethyl-3-methylimidazolium chloride, and 1-ethyl-3-methylimidazolium bromide. However, the halide represented by the chemical formula (E) is not limited to these compounds. <Phosphorus Compounds Produced in Step (II)> The phosphorus compound produced in the step (II) is represented by the following chemical formula (F) or (G).

[0147] [ka]

[0148] [ka]

[0149] In the chemical formula (F), 4 , R 6 , X, and n are all the same as those in the chemical formulas (C') and (E), and therefore, details thereof will be omitted.

[0150] Specific examples of the chemical formula (F) are the same as those described in the chemical formula (C) except for the case where M is hydrogen, and therefore will not be repeated here.

[0151] In the chemical formula (G), the M′ and Y 2 , Y 3 , Z, and n are all the same as those in the chemical formulas (D) and (E), and therefore, details thereof will be omitted.

[0152] Specific examples of the phosphorus compound represented by the chemical formula (G) include 1,3,2-dioxaphospholane-2-hydroxy-2-oxide lithium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide lithium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide sodium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide potassium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide magnesium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide calcium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide aluminum, and 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide tin. , 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide copper, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide silver, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide tetramethylammonium, 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide 1-ethyl-3-methylimidazolium, 1,3,2-dithiaphospholane-2-hydroxy-2-oxide lithium, 1,3,2-diazaphosphoridine-2-hydroxy-2-oxide lithium, 1,3,2-benzodioxaphosphole-2-hydroxy-2-oxide lithium, 4H-1,3,2-benzodioxaphosphorin-4-one-2-hydroxy-2-oxide lithium, etc. However, the phosphorus compound represented by the chemical formula (G) is not limited to these compound groups.

[0153] <Reaction conditions for step (II)> The molar ratio of the reaction in step (II) is not particularly limited and may be appropriately set depending on the reactants. Regarding the molar ratio of the reaction between the phosphoric acid compound represented by chemical formula (C') or (D) and the salt of the cation and anion represented by chemical formula (E), the amount of the salt of the cation and anion represented by chemical formula (E) is preferably in the range of 0.1 to 2.5 moles per mole of the phosphoric acid compound represented by chemical formula (C') or (D), and from the viewpoints of removing raw material residues and suppressing by-products, the amount is more preferably in the range of 0.3 to 2.0 moles, and particularly preferably in the range of 0.5 to 1.5 moles.

[0154] The reaction initiation temperature in the step (II) is not particularly limited as long as the reaction proceeds, and may be appropriately set depending on the reactants. The reaction initiation temperature is preferably in the range of -20°C to 150°C, more preferably in the range of 0°C to 100°C, and particularly preferably in the range of 25°C to 50°C, from the viewpoints of improving reactivity and suppressing excess energy.

[0155] The means for adjusting the reaction initiation temperature is not particularly limited. For example, when the reaction initiation temperature is controlled by cooling so that it falls within the above-mentioned temperature range, an ice bath or the like can be used to place the reaction vessel into which the phosphoric acid compound represented by the chemical formula (C') or (D) and the salt composed of a cation and an anion represented by the chemical formula (E) are added. When the reaction initiation temperature is controlled by heating so that it falls within the above-mentioned temperature range, an oil bath or the like set at a desired temperature can be used.

[0156] The reaction time of the step (II) is not particularly limited and may be appropriately set depending on the reactant species. The lower limit of the reaction time is usually 1 hour or more. The upper limit of the reaction time is usually 12 hours or less, and from the viewpoint of industrial production, 6 hours or less is preferable, and 3 hours or less is more preferable.

[0157] The reaction in step (II) can be carried out without a solvent or in a solvent. When the reaction in step (II) is carried out without a solvent, the phosphoric acid compound represented by chemical formula (C') or (D) also functions as a reaction solvent.

[0158] The solvent is not particularly limited as long as it does not cause any problems such as reacting with other reactants or products.

[0159] The solvent is not particularly limited, and examples thereof include water, alcohols, nitriles, esters, ketones, ethers, halogenated hydrocarbons, etc. These may be used alone or in combination of two or more.

[0160] The alcohols are not particularly limited, and examples thereof include methanol, ethanol, propanol, 2-propanol, butanol, pentanol, hexanol, heptanol, octanol, 2-iodoethanol, 2-bromoethanol, 2-chloroethanol, 2-fluoroethanol, 1,2-diiodoethanol, 1,2-dibromoethanol, 1,2-dichloroethanol, 1,2-difluoroethanol, 2,2-diiodoethanol, 2,2-dibromoethanol, 2,2-dichloroethanol, 2,2-difluoroethanol, 2,2,2-tribromoethanol, 2,2,2-trichloroethanol, 2,2,2-trifluoroethanol, hexafluoro-2-propanol, etc. These may be used alone or in combination of two or more.

[0161] The nitriles, esters, ketones, ethers, and halogenated hydrocarbons may be the same as those used in the non-aqueous solvent described in step (I), and therefore, further details thereof will be omitted.

[0162] The lower limit of the amount of the solvent used is preferably 1 mole or more, more preferably 10 moles or more, per mole of the phosphoric acid compound represented by chemical formula (C') or (D). The upper limit of the amount of the solvent used is preferably 10,000 moles or less, more preferably 1,000 moles or less, and even more preferably 100 moles or less, per mole of the phosphoric acid ester represented by chemical formula (C') or (D). By setting the lower limit of the amount of the solvent to 1 mole or more, a decrease in the reactivity between the phosphoric acid compound represented by chemical formula (C') or (D) and the salt of a cation and anion represented by chemical formula (E) can be prevented, and a decrease in the yield and purity of the phosphorus compound represented by chemical formula (F) or (G) can be suppressed. On the other hand, by setting the upper limit of the amount of the solvent used to 10,000 moles or less, the energy required for distilling off the solvent can be reduced, preventing disadvantages in industrial production.

[0163] The phosphorus compound represented by the chemical formula (F) or (G) obtained in the step (II) may be isolated and purified depending on its purity. The method for isolating and purifying it is not particularly limited, and known methods can be used. Specific examples include atmospheric distillation, reduced pressure distillation, filtration, filtration, recrystallization, sublimation purification, silica gel column chromatography, preparative thin layer chromatography (PTLC), high performance liquid chromatography (HPLC), and ion chromatography (IC). [Example]

[0164] Preferred examples of the present invention will be described in detail below. However, the materials and blending amounts described in these examples are not intended to limit the scope of the present invention.

[0165] In the following examples, the determination of purity and the measurement of physicochemical properties were carried out using the following apparatuses.

[0166] (purity) The purity of the phosphorus compound was calculated from the relative area ratio (%) by anion analysis using ion chromatography. The analytical equipment and measurement conditions were as follows: Equipment: 850 Professional IC Anion (Metrohm) Column: Dionex IonPac AS23 2x250mm (Thermo Fisher Scientific) Sample: 100 ppm sample aqueous solution Flow rate: 1mL / min Eluent: 4.5 mM Na2CO3 in a 7:3 mixture of H2O and acetonitrile

[0167] (qualitative) The quality of the phosphorus compounds was determined by mass spectrometry using a benchtop nuclear magnetic resonance spectrometer (hereinafter referred to as "NMR") or a liquid chromatograph mass spectrometer (hereinafter referred to as "LC / MS"). The analytical equipment and measurement conditions are as follows: (NMR measurement) Tabletop Nuclear Magnetic Resonance Analyzer: Spinsolve 60 ULTRA Phosphorus (Magritek)

[0168] (mass spectrometry) Liquid chromatograph mass spectrometer: ACQUITY UPLC H-Class / SQ Detector 2 (manufactured by Waters) Column: ACQUITY UPLC BEH C18 2.1x50mm (Waters) Sample: 100 ppm sample aqueous solution Flow rate: 0.5mL / min Eluent A: 0.1% formic acid aqueous solution Eluent B: 0.1% formic acid in acetonitrile Gradient analysis: Eluent A / Eluent B = 90 / 10 to 60 / 40

[0169] Example 1 <Synthesis of 2,2,2-trifluoroethyl monofluorophosphate> Trimethylsilyl difluorophosphate (3.00 g, 17.2 mmol, in-house product) was placed in a 50 mL eggplant-shaped flask equipped with a stir bar. While stirring with a stirrer, 2,2,2-trifluoroethanol (2.58 g, 25.8 mmol, TCI) was gradually added at room temperature. The mixture was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 2.70 g of 2,2,2-trifluoroethyl monofluorophosphate as a colorless liquid. The purity of the 2,2,2-trifluoroethyl monofluorophosphate was 78.8%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 181.1, corresponding to the mass of the 2,2,2-trifluoroethyl monofluorophosphate anion.

[0170] Example 2 <Synthesis of (2,2,2-trifluoroethyl)lithium monofluorophosphate> A 100 mL beaker containing a stirrer was charged with 2,2,2-trifluoroethyl monofluorophosphate (2.40 g, 13.2 mmol) prepared in Example 1 and 40 mL of water. While stirring with a stirrer, lithium carbonate (Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 13 g of DME were charged into another 100 mL beaker containing a stirrer, and the mixture was stirred for 30 minutes. The insoluble matter was then filtered to obtain 0.6 g of lithium 2,2,2-trifluoroethyl monofluorophosphate as a white solid. The purity of the lithium 2,2,2-trifluoroethyl monofluorophosphate was 95.5%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 181.1, corresponding to the mass of the 2,2,2-trifluoroethyl monofluorophosphate anion.

[0171] Example 3 <Synthesis of propargyl monofluorophosphate> Trimethylsilyl difluorophosphate (3.00 g, 17.2 mmol, manufactured by our company) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer, and then propargyl alcohol (1.06 g, 18.9 mmol, manufactured by TCI) was gradually added at room temperature while stirring with a stirrer. This mixture was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 2.50 g of propargyl monofluorophosphate as a colorless liquid. The purity of the propargyl monofluorophosphate was 81.8%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 137.1, corresponding to the mass of propargyl monofluorophosphate anion.

[0172] Example 4 <Synthesis of propargyl lithium monofluorophosphate> A 200 mL beaker containing a stirrer was charged with propargyl monofluorophosphate (2.40 g, 17.4 mmol) prepared in Example 3 and 60 mL of water. While stirring with a stirrer, lithium carbonate (Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 19 g of DME were placed in another 100 mL beaker containing a stirrer and stirred for 30 minutes. The insoluble matter was then filtered off to obtain a white solid. Furthermore, this solid and 88 g of ethanol were placed in another 200 mL beaker containing a stirrer and stirred for 15 minutes. The insoluble matter was then filtered off, and the solvent was concentrated using an evaporator to obtain 1.6 g of lithium monofluorophosphate propargyl as a white solid. The purity of the lithium monofluorophosphate propargyl was 95.1%. LC / MS (negative mode) was measured, and a mass spectrum was obtained with a main peak at m / z=137.1, which corresponds to the mass of monofluorophosphate propargyl anion.

[0173] Example 5 <Synthesis of phenyl monofluorophosphate> Phenol (1.03 g, 10.9 mmol, Wako Pure Chemical Industries, Ltd.) and 30 mL of toluene were placed in a 100 mL eggplant-shaped flask equipped with a stirrer. Trimethylsilyl difluorophosphate (2.05 g, 11.8 mmol, in-house product) was gradually added at room temperature while stirring with a stirrer. This mixture was heated and refluxed at 110°C for 2 hours under a nitrogen stream. After allowing the reaction mixture to cool to room temperature, it was concentrated using an evaporator to obtain 1.93 g of phenyl monofluorophosphate as a pale yellow oily liquid. The purity of the phenyl monofluorophosphate was 88.9%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 175.2, corresponding to the mass of the phenyl monofluorophosphate anion.

[0174] Example 6 <Synthesis of phenyllithium monofluorophosphate> Phenyl monofluorophosphate (1.11 g, 6.30 mmol) prepared in Example 5 and 12 mL of water were placed in a 100 mL beaker containing a stirrer. While stirring with a stirrer, lithium carbonate (222 mg, 3.00 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 30 mL of hexane were placed in another 100 mL beaker containing a stirrer, and the mixture was stirred for 15 minutes. The insoluble matter was then filtered off. This procedure was repeated two more times to obtain 960 mg of white solid phenyllithium monofluorophosphate. The purity of the phenyllithium monofluorophosphate was 88.8%. NMR analysis revealed NMR spectra corresponding to phenyllithium monofluorophosphate. 1 H-NMR(CD3OD,δppm):6.75-7.50(m,5H); 19 F-NMR(CD3OD,δppm):-76.32(d,1F,J P-F =931.4Hz); 31 P-NMR(CD3OD,δppm):-13.02(d,1P,J P-F =931.4Hz)

[0175] Example 7 <Synthesis of methyl monofluorophosphate> Trimethylsilyl difluorophosphate (2.00 g, 11.5 mmol, manufactured by our company) was placed in a 20 mL eggplant-shaped flask equipped with a stirrer, and then methanol (370 mg, 11.5 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixed solution was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 1.18 g of methyl monofluorophosphate as a colorless liquid. The purity of the methyl monofluorophosphate was 89.7%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 113.1, corresponding to the mass of the methyl monofluorophosphate anion.

[0176] Example 8 <Synthesis of methyllithium monofluorophosphate> Methyl monofluorophosphate (1.82 g, 16.0 mmol) prepared in Example 7 and 16 mL of water were placed in a 100 mL beaker containing a stirrer. While stirring with a stirrer, lithium carbonate (922 mg, 12.5 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 30 mL of DME were placed in another 100 mL beaker containing a stirrer and stirred for 30 minutes. The insoluble matter was filtered and washed with a small amount of ethanol (1 mL x 3), obtaining a white solid. Furthermore, this solid and 300 mL of ethanol were placed in another 500 mL beaker containing a stirrer and stirred for 15 minutes. The insoluble matter was filtered off, and the solvent was concentrated using an evaporator to obtain 1.34 g of methyllithium monofluorophosphate as a white solid. The purity of methyllithium monofluorophosphate was 94.7%. NMR was measured, and the NMR spectrum corresponding to methyllithium monofluorophosphate was obtained. 1 H-NMR (DO, δ ppm): 3.70 (d, 3H, J P-H =11.3Hz); 19 F-NMR (DO, δ ppm): -80.6 (d, 1F, J P-F =928.8Hz); 31 P-NMR(D2O,δppm):-4.11(dq,1P,J P-F =928.8Hz,J P-H =11.3Hz)

[0177] Example 9 <Synthesis of ethyl monofluorophosphate> Trimethylsilyl difluorophosphate (2.00 g, 11.5 mmol, manufactured by our company) was placed in a 20 mL eggplant-shaped flask equipped with a stirrer, and then ethanol (550 mg, 11.9 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixed solution was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 1.43 g of ethyl monofluorophosphate as a colorless liquid. The purity of the ethyl monofluorophosphate was 95.1%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 127.1, corresponding to the mass of the ethyl monofluorophosphate anion.

[0178] Example 10 <Synthesis of isopropyl monofluorophosphate> Trimethylsilyl difluorophosphate (2.00 g, 11.5 mmol, manufactured by our company) was placed in a 20 mL eggplant-shaped flask equipped with a stirrer, and then isopropanol (699 mg, 11.6 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixed solution was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 1.49 g of isopropyl monofluorophosphate as a colorless liquid. The purity of the isopropyl monofluorophosphate was 97.0%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 141.1, corresponding to the mass of the isopropyl monofluorophosphate anion.

[0179] Example 11 <Synthesis of isopropyllithium monofluorophosphate> In a 100 mL beaker containing a stirrer, the isopropyl monofluorophosphate (2.22 g, 15.6 mmol) prepared in Example 10 and 16 mL of water were placed. While stirring with a stirrer, lithium carbonate (786 mg, 10.6 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 30 mL of DME were placed in another 100 mL beaker containing a stirrer, and after stirring for 30 minutes, the insoluble matter was filtered off and washed with a small amount of ethanol (1 mL x 3), obtaining a white solid. Furthermore, this solid and 300 mL of ethanol were placed in another 500 mL beaker containing a stirrer, and after stirring for 15 minutes, the insoluble matter was filtered off. The solvent was concentrated using an evaporator to obtain 1.22 g of lithium isopropyl monofluorophosphate as a white solid. The purity of isopropyllithium monofluorophosphate was 97.2%. NMR was measured, and NMR spectra corresponding to isopropyllithium monofluorophosphate were obtained. 1 H-NMR (DO, δ ppm): 1.30 (d, 6H, J P-H =6.2Hz), 4.06-5.22(m,1H); 19 F-NMR (DO, δ ppm): -74.9 (d, 1F, J P-F =925.7Hz); 31 P-NMR(D2O,δppm):-5.86(dd,1P,J P-F =925.7Hz,J P-H =7.1Hz)

[0180] Example 12 <Synthesis of allyl monofluorophosphate> Trimethylsilyl difluorophosphate (4.02 g, 23.1 mmol, manufactured by our company) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer, and then allyl alcohol (1.22 g, 21.0 mmol, manufactured by TCI) was gradually added at room temperature while stirring with a stirrer. This mixture was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 2.94 g of allyl monofluorophosphate as a colorless liquid. The purity of the allyl monofluorophosphate was 85.3%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 139.2, corresponding to the mass of allyl monofluorophosphate anion.

[0181] Example 13 <Synthesis of allyllithium monofluorophosphate> In a 100 mL beaker containing a stirrer, allyl monofluorophosphate (2.94 g, 21.0 mmol) prepared in Example 12 and 21 mL of water were placed. While stirring with a stirrer, lithium carbonate (987 mg, 13.4 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 20 mL of DME were placed in another 100 mL beaker containing a stirrer, and after stirring for 15 minutes, the insoluble matter was filtered off and washed with a small amount of ethanol (1 mL x 2), obtaining a white solid. Furthermore, this solid and 300 mL of ethanol were placed in a 500 mL beaker containing a stirrer, and after stirring for 15 minutes, the insoluble matter was filtered off. The solvent was concentrated using an evaporator to obtain 1.60 g of lithium allyl monofluorophosphate as a white solid. The purity of allyllithium monofluorophosphate was 95.9%. NMR was measured, and NMR spectra corresponding to allyllithium monofluorophosphate were obtained. 1 H-NMR(D2O,δppm):4.34-4.65(m,2H),5.14-5.58(m,2H),5.74-6.36(m,1H); 19 F-NMR (DO, δ ppm): -77.0 (d, 1F, J P-F=930.4Hz); 31 P-NMR(D2O,δppm):-5.31(dt,1P,J P-F =930.4Hz,J P-H =8.9Hz)

[0182] Example 14 <Synthesis of 2-(2-(2-methoxyethoxy)ethoxy)ethyl monofluorophosphate> Trimethylsilyl difluorophosphate (3.20 g, 18.4 mmol, in-house product) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer. Triethylene glycol monomethyl ether (2.72 g, 16.6 mmol, TCI) was then slowly added at room temperature while stirring. The mixture was heated at 60 °C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 4.08 g of 2-(2-(2-methoxyethoxy)ethoxy)ethyl monofluorophosphate as a colorless liquid. The purity of the 2-(2-(2-methoxyethoxy)ethoxy)ethyl monofluorophosphate was 75.6%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 245.3, corresponding to the mass of the 2-(2-(2-methoxyethoxy)ethoxy)ethyl monofluorophosphate anion.

[0183] Example 15 <Synthesis of (2-(2-(2-methoxyethoxy)ethoxy)ethyl)lithium monofluorophosphate> In a 100 mL beaker containing a stirrer, 2-(2-(2-methoxyethoxy)ethoxy)ethyl monofluorophosphate (4.08 g, 16.6 mmol) prepared in Example 14 and 17 mL of water were placed, and while stirring with a stirrer, lithium carbonate (932 mg, 12.6 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and then the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 150 mL of DME were placed in another 300 mL beaker containing a stirrer, and after stirring for 15 minutes, the insoluble matter was filtered off to obtain a white solid. Furthermore, this solid and 500 mL of ethanol were placed in another 1000 mL beaker containing a stirrer and stirred for 15 minutes. After that, the insoluble matter was filtered off and the solvent was concentrated using an evaporator to obtain 2.73 g of (2-(2-(2-methoxyethoxy)ethoxy)ethyl)lithium monofluorophosphate as a white solid. The purity of (2-(2-(2-methoxyethoxy)ethoxy)ethyl)lithium monofluorophosphate was 95.7%. NMR was measured and NMR spectra corresponding to (2-(2-(2-methoxyethoxy)ethoxy)ethyl)lithium monofluorophosphate were obtained. 1 H-NMR(D2O,δppm):3.38(br s,3H),3.65-3.82(br m,10H),3.98-4.27(br m,2H); 19 F-NMR (DO, δ ppm): -77.6 (d, 1F, J P-F =930.0Hz); 31 P-NMR(D2O,δppm):-5.33(dt,1P,J P-F =930.0Hz,J P-H =7.2Hz)

[0184] Example 16 <Synthesis of (2-oxo-1,3-dioxolan-4-yl)methyl monofluorophosphate> Trimethylsilyl difluorophosphate (3.23 g, 18.5 mmol, in-house production) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer. Then, while stirring with a stirrer, 4-hydroxymethyl-2-oxo-1,3-dioxolane (2.00 g, 16.7 mmol, TCI) was gradually added at room temperature. The resulting mixture was heated at 60°C for 2 hours under a nitrogen stream. After allowing the reaction mixture to cool to room temperature, it was concentrated using an evaporator to obtain 3.38 g of a colorless liquid, 2-oxo-1,3-dioxolan-4-yl methyl monofluorophosphate. The purity of the 2-oxo-1,3-dioxolan-4-yl methyl monofluorophosphate was 83.4%. LC / MS (negative mode) was measured, and a mass spectrum was obtained with a main peak at m / z=199.2, which corresponds to the mass of methyl monofluorophosphate (2-oxo-1,3-dioxolan-4-yl) anion.

[0185] Example 17 <Synthesis of (2-oxo-1,3-dioxolan-4-yl)methyllithium monofluorophosphate> A 100 mL beaker containing a stirrer was charged with (2-oxo-1,3-dioxolan-4-yl)methyl monofluorophosphate (3.30 g, 16.5 mmol) prepared in Example 16 and 16 mL of water. While stirring with a stirrer, lithium carbonate (1.22 g, 16.5 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 17 mL of DME were placed in another 100 mL beaker containing a stirrer and stirred for 15 minutes. The insoluble matter was filtered off and washed with a small amount of ethanol (3 mL x 3), obtaining a white solid. Furthermore, this solid and 500 mL of ethanol were placed in another 1000 mL beaker containing a stirrer and stirred for 15 minutes. The insoluble matter was filtered off, and the solvent was concentrated using an evaporator to obtain a white solid. For further purification, the solid was ground in a mortar and pestle, then washed with DME and filtered four times to obtain 928 mg of (2-oxo-1,3-dioxolan-4-yl)methyllithium monofluorophosphate as a white solid. The purity of (2-oxo-1,3-dioxolan-4-yl)methyllithium monofluorophosphate was 96.1%. NMR analysis yielded NMR spectra corresponding to (2-oxo-1,3-dioxolan-4-yl)methyllithium monofluorophosphate. 1 H-NMR(D2O,δppm):4.27-5.14(br m,5H); 19 F-NMR (DO, δ ppm): -77.7 (d, 1F, J P-F =932.8Hz); 31 P-NMR(D2O,δppm):-6.05(dt,1P,J P-F =932.8Hz,J P-H =6.9Hz)

[0186] Example 18 <Synthesis of 1,1,1,3,3,3-hexafluoro-2-propyl monofluorophosphate> Trimethylsilyl difluorophosphate (3.01 g, 17.3 mmol, in-house production) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer, and then 1,1,1,3,3,3-hexafluoro-2-propanol (4.38 g, 26.1 mmol, Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixture was heated at 130 °C for 24 hours under an argon atmosphere. After allowing the reaction mixture to cool to room temperature, it was concentrated using an evaporator to obtain 2.50 g of 1,1,1,3,3,3-hexafluoro-2-propyl monofluorophosphate as a colorless liquid. The purity of the 1,1,1,3,3,3-hexafluoro-2-propyl monofluorophosphate was 76.2%. LC / MS (negative mode) was measured, and a mass spectrum was obtained with a main peak at m / z=249.2, which corresponds to the mass of monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) anion.

[0187] Example 19 <Synthesis of lithium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl)> In a 100 mL beaker containing a stirrer, 1,1,1,3,3,3-hexafluoro-2-propyl monofluorophosphate (2.50 g, 10.0 mmol) prepared in Example 18 and 10 mL of water were placed. While stirring with a stirrer, lithium carbonate (703 mg, 9.51 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 18 mL of ethanol were placed in another 100 mL beaker containing a stirrer and stirred for 15 minutes. After that, insoluble matter was filtered off, and the solvent was concentrated using an evaporator to obtain a white solid. The solid was then washed with DMC and collected by filtration to obtain 1.27 g of lithium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) as a white solid. The purity of the lithium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) was 97.0%. NMR was measured, and the NMR spectra corresponding to lithium monofluorophosphate (1,1,1,3,3,3-hexafluoro-2-propyl) were obtained. 1 H-NMR(D2O,δppm):3.86(br s,1H); 19 F-NMR (DO, δ ppm): -74.5 (d, 1F, J P-F =948.9Hz),-73.9(br s,6F); 31 P-NMR(D2O,δppm):-9.18(dd,1P,J P-F =948.9Hz,J P-H =12.4Hz)

[0188] Example 20 <Synthesis of methylcesium monofluorophosphate> Trimethylsilyl difluorophosphate (2.07 g, 11.9 mmol, manufactured by our company) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer, and then methanol (572 mg, 17.8 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixed solution was heated at 60 °C for 2 hours under a nitrogen stream. After allowing the reaction mixture to cool to room temperature, it was concentrated using an evaporator to obtain methyl monofluorophosphate as a colorless liquid. This methyl monofluorophosphate (1.35 g, 11.8 mmol) and 10 mL of water were placed in a 100 mL beaker equipped with a stirrer, and while stirring with a stirrer, cesium carbonate (2.76 g, 8.47 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added until the pH became neutral. The reaction solution was filtered, and the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 30 mL of DME were placed in a 100 mL beaker equipped with a stir bar and stirred for 15 minutes. The insoluble matter was then filtered off to obtain a white solid. Furthermore, this solid and 150 mL of ethanol were placed in a 300 mL beaker equipped with a stir bar and stirred for 15 minutes. The insoluble matter was then filtered off, and the solvent was concentrated using an evaporator. This procedure was repeated once more to obtain 1.49 g of methylcesium monofluorophosphate as a white solid. The purity of the methylcesium monofluorophosphate was 86.0%. NMR analysis yielded NMR spectra corresponding to methylcesium monofluorophosphate. 1 H-NMR (DO, δ ppm): 3.74 (d, 3H, J P-H =11.2Hz); 19 F-NMR (DO, δ ppm): -80.4 (d, 1F, J P-F =928.6Hz); 31 P-NMR(D2O,δppm):-4.08(dq,1P,J P-F =928.6Hz,J P-H =11.2Hz)

[0189] Example 21 <Synthesis of cesium (2,2,2-trifluoroethyl) monofluorophosphate> Trimethylsilyl difluorophosphate (4.50 g, 25.8 mmol, manufactured by our company) was placed in a 50 mL eggplant-shaped flask equipped with a stir bar, and then 2,2,2-trifluoroethanol (1.70 g, 17.0 mmol, manufactured by TCI) was gradually added at room temperature while stirring with a stirrer. This mixture was heated at 60 °C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 2,2,2-trifluoroethyl monofluorophosphate as a colorless liquid. This 2,2,2-trifluoroethyl monofluorophosphate (3.10 g, 17.0 mmol) and 10 mL of water were placed in a 100 mL beaker equipped with a stir bar, and cesium carbonate (3.50 g, 10.7 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added while stirring with a stirrer until the pH became neutral. The reaction solution was filtered, and then the reaction solvent was concentrated using an evaporator to obtain a white solid. This solid and 30 g of DMC were placed in a 100 mL beaker equipped with a stirring bar, and after stirring for 15 minutes, the insoluble matter was filtered off. This procedure was repeated once more to obtain 4.21 g of cesium monofluorophosphate (2,2,2-trifluoroethyl) as a white solid. The purity of the cesium monofluorophosphate (2,2,2-trifluoroethyl) was 97.0%. NMR analysis yielded NMR spectra corresponding to cesium monofluorophosphate (2,2,2-trifluoroethyl). 1 H-NMR (DO, δ ppm): 4.53 (p, 2H, J P-H =8.7Hz,J F-H =8.6Hz); 19 F-NMR(D2O,δppm):-76.3(dd,1F,J F-H =8.6Hz,J F-F =1.9Hz), -73.3(td,3F,J P-F =937.8Hz,J F-F =1.9Hz); 31 P-NMR(D2O,δppm):-6.92(dt,1P,J P-F =937.8Hz,J P-H =8.7Hz)

[0190] Example 22 <Synthesis of ethylphenyl phosphate> Phenyltrimethylsilyl monofluorophosphate (1.80 g, 7.25 mmol, in-house production) was placed in a 50 mL eggplant-shaped flask equipped with a stirrer, and then ethanol (0.67 g, 14.5 mmol, Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixture was heated at 80°C for 2 hours under an argon atmosphere. After allowing the reaction mixture to cool to room temperature, it was concentrated using an evaporator to obtain 1.46 g of ethylphenyl phosphate as a colorless liquid. The purity of the ethylphenyl phosphate was 76.8%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 201.2, corresponding to the mass of the ethylphenyl phosphate anion.

[0191] Example 23 <Synthesis of 2-fluorophosphonooxyethyl monofluorophosphate> Trimethylsilyl difluorophosphate (4.00 g, 23.0 mmol, in-house product) was placed in a 20 mL eggplant-shaped flask equipped with a stirrer, and then ethylene glycol (711 mg, 11.5 mmol, Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature while stirring with a stirrer. This mixture was heated at 60°C for 2 hours under a nitrogen stream. The reaction mixture was allowed to cool to room temperature and then concentrated using an evaporator to obtain 2.32 g of 2-fluorophosphonooxyethyl monofluorophosphate as a reddish-brown liquid. The purity of the 2-fluorophosphonooxyethyl monofluorophosphate was 74.1%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 225.0, corresponding to the mass of the 2-fluorophosphonooxyethyl monofluorophosphate anion.

[0192] Example 24 <Synthesis of 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide> Trimethylsilyl difluorophosphate (4.01 g, 23.0 mmol, manufactured by our company) was placed in a 20 mL eggplant-shaped flask equipped with a stirrer. While stirring with a stirrer, propane-1,3-diol (1.75 g, 23.0 mmol, manufactured by Wako Pure Chemical Industries, Ltd.) was gradually added at room temperature. This mixture was heated at 60 °C for 2 hours under a nitrogen stream. LC / MS (negative mode) analysis confirmed the mass spectrum with a main peak at m / z = 157.0, corresponding to the mass of the monofluorophosphate (3-hydroxypropyl) anion. After allowing the reaction mixture to cool to room temperature, chlorotrimethylsilane (2.57 g, 23.7 mmol, manufactured by TCI) was added to the reaction mixture and stirred with a stirrer to prepare trimethylsilyl difluorophosphate (3-hydroxypropyl). This mixture was again heated at 60 °C for 2 hours under a nitrogen stream. The reaction mixture was concentrated using an evaporator to obtain 3.11 g of 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide. The purity of the 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide was 71.7%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 137.0, corresponding to the mass of the 1,3,2-dioxaphosphorinane-2-hydroxy-2-oxide anion.

[0193] Example 25 <Synthesis of methyllithium monofluorophosphate> Lithium methoxide (437 mg, 11.5 mmol, Sigma-Aldrich) and 11.5 mL of acetonitrile were placed in a 50 mL eggplant-shaped flask equipped with a stirrer. Then, while stirring with a stirrer, trimethylsilyl difluorophosphate (2.06 g, 11.8 mmol, in-house product) was gradually added at room temperature. The mixture was heated at 60 °C for 2 hours under a nitrogen stream. After allowing the reaction mixture to cool to room temperature, the acetonitrile-insoluble material was collected by suction filtration and washed five times with 10 mL of acetonitrile to obtain 0.42 g of a white solid, methyllithium monofluorophosphate. The purity of the methyllithium monofluorophosphate was 74.5%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 113.1, corresponding to the mass of the methyl monofluorophosphate anion.

[0194] Example 26 <Synthesis of phenyllithium monofluorophosphate> Lithium phenoxide (1.16 g, 11.6 mmol, in-house product) and 11.5 mL of acetonitrile were placed in a 50 mL eggplant-shaped flask equipped with a stirrer. Then, while stirring with a stirrer, trimethylsilyl difluorophosphate (2.13 g, 12.2 mmol, in-house product) was gradually added at room temperature. This mixture was heated at 60 °C for 2 hours under a nitrogen stream. After allowing the reaction mixture to cool to room temperature, the insoluble matter in acetonitrile was collected by suction filtration and washed four times with 10 mL of acetonitrile to obtain 0.68 g of white solid phenyllithium monofluorophosphate. The purity of the phenyllithium monofluorophosphate was 82.1%. LC / MS (negative mode) analysis yielded a mass spectrum with a main peak at m / z = 175.2, corresponding to the mass of the phenyl monofluorophosphate anion. [Industrial Applicability]

[0195] The phosphorus compounds obtained by the production method of the present invention are expected to be used in a wide variety of applications, such as water and oil repellent treatment agents for fibers, paper, etc., surfactants, release agents, metal surface treatment agents, resin curing agents, lubricating oil additives, antistatic agents, flame retardants, rust inhibitors for greases, cosmetics, oral preparations, and additives for non-aqueous electrolytes for secondary batteries.

Claims

1. A method for producing a phosphorus compound represented by the following chemical formula (C), comprising step (I) of reacting a phosphate silyl ester represented by the following chemical formula (A) with a compound represented by the following chemical formula (B): 【Chemistry 1】 [Wherein, R １ ~R ３ are each independently a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond, or an alkoxy group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond. １ R ４ group, or -Y ２ -Z-Y ３ represents a H group. １ ~Y ３ are each independently an oxygen atom, a sulfur atom, or an imino group (NR ５ ) and the R ４ , and R ５ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond, and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond.] 【Chemistry 2】 [Wherein, R ６ represents a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond; ４ is an oxygen atom, a sulfur atom, or an imino group (NR ７ ) and the R ７ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a heteroatom, or an unsaturated bond, and M represents a hydrogen atom, an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium. The n represents the valence of the cation. 【Transformation 3】 [Wherein, M and Y ４ , R ６ , X, and n are the same as those in the chemical formulas (A) and (B).

2. The R １ ~R ３ The method according to claim 1 , wherein all of are methyl groups.

3. The Y ４ is an oxygen atom, the R ６ The method according to claim 1 , wherein M is an alkyl group or a phenyl group, and M is a hydrogen atom.

4. The production method according to claim 1, wherein the compound represented by chemical formula (B) is methanol, ethanol, 2-propanol, butanol, 2,2,2-trifluoroethanol, 1,1,1,3,3,3-hexafluoro-2-propanol, allyl alcohol, propargyl alcohol, phenol, 4-hydroxymethyl-2-oxo-1,3-dioxolane, triethylene glycol monomethyl ether, ethylene glycol, or propane-1,3-diol.

5. The Y ４ is an oxygen atom, the R ６ The method according to claim 1, wherein is an alkyl group or a phenyl group, and M is an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium.

6. 2. The method according to claim 1, wherein the compound represented by chemical formula (B) is lithium methoxide, sodium methoxide, potassium methoxide, lithium ethoxide, sodium ethoxide, potassium ethoxide, lithium phenoxide, or sodium phenoxide.

7. The Y ２ , and Y ３ The method according to claim 1 , wherein is an oxygen atom and Z is a trimethylene group.

8. The method according to claim 1 , wherein step (I) is carried out in the absence of a solvent.

9. The method according to claim 1 , wherein the step (I) is carried out in a non-aqueous solvent.

10. The method according to claim 9 , wherein the non-aqueous solvent is an aprotic organic solvent.

11. A method for producing a phosphoric acid compound represented by the following chemical formula (D), comprising a step (I') of intramolecularly reacting a phosphoric acid silyl ester represented by the following chemical formula (A'): 【Chemistry 4】 [Wherein, R １ ~R ３ each independently represents a hydrogen atom, a halogen atom, a hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, or an unsaturated bond, or an alkoxy group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, or an unsaturated bond. ２ and Y ３ are each independently an oxygen atom, a sulfur atom, or an imino group (NR ５ ), and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond.] 【Transformation 5】 [Wherein, the Y ２ , Y ３ , Z are the same as those in the chemical formula (A').

12. The Y ２ , and Y ３ The method according to claim 11, wherein Z is an oxygen atom and Z is a trimethylene group.

13. A method for producing a phosphorus compound represented by the following chemical formula (F) or chemical formula (G), comprising step (II) of reacting a phosphorus compound represented by the following chemical formula (C') or a phosphorus compound represented by the following chemical formula (D) with a salt consisting of a cation and an anion represented by the following chemical formula (E). 【Transformation 6】 [Wherein, R ６ represents a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond; ４ is an oxygen atom, a sulfur atom, or an imino group (NR ７ ) and the R ７ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and at least one of a halogen atom, a hetero atom, and an unsaturated bond. １ R ４ group, or -Y ２ -Z-Y ３ represents a H group. １ ~Y ３ are each independently an oxygen atom, a sulfur atom, or an imino group (NR ５ ) and the R ４ , and R ５ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond, and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond.] 【Transformation 7】 [Wherein, the Y ２ and Y ３ are each independently an oxygen atom, a sulfur atom, or an imino group (NR ５ ) and the R ５ represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond, and Z represents a divalent hydrocarbon group having 1 to 20 carbon atoms, or a divalent hydrocarbon group having 1 to 20 carbon atoms and having at least one of a halogen atom, a hetero atom, or an unsaturated bond.] 【Transformation 8】 [wherein M′ represents an alkali metal, an alkaline earth metal, aluminum, a transition metal, or an onium, and Q represents a hydroxide, a carbonate, a hydrogen carbonate, an oxide, or a halogen atom. The n represents the valence of the cation, and the m represents the valence of the anion. 【Chemistry 9】 [wherein M′ and Y ４ , R ６ , X, and n are the same as those in the chemical formulas (C') and (E). 【Chemistry 10】 [wherein M′ and Y ２ , Y ３ , Z, and n are the same as those in the chemical formulas (D) and (E).

14. 14. The method according to claim 13, wherein M' is a lithium atom, a sodium atom, a potassium atom, a cesium atom, a calcium atom, a magnesium atom, an aluminum atom, a copper atom, a silver atom, a tin atom, tetramethylammonium, tetraethylammonium, triethylmethylammonium, tributylmethylammonium, 1-methyl-3-propylpyrrolidinium, or 1-ethyl-3-methylimidazolium.

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